JP3133737B2 - Electro-optical liquid crystal system - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

FIELD OF THE INVENTION The present invention comprises: a dielectrically positive liquid crystal mixture and also an optically transparent medium between two electrodes optionally provided on a support sheet, the liquid crystal molecules being switched off. One of the refractive indices of the liquid crystal mixture essentially corresponds to the refractive index nM of the optically transparent medium and / or the mass of the liquid crystal mixture is optically transparent. The value divided by the mass of the medium is 1.
5 or more, and irrespective of the polarization of the incident light, to an electro-optical liquid-crystal system having a reduced transmission in one of the two switching states compared to the other, and to the liquid-crystal mixtures used in this system.

[0002]

BACKGROUND OF THE INVENTION Depending on the mass of a liquid crystal mixture in a system, this mixture can be embedded in an optically transparent medium in the form of more or less demarcated liquid crystal microdroplets, or else the optical A transparent medium can form a somewhat cohesive continuous phase, for example present in the form of particles.
The continuous phase is also obtained, for example, when the optically transparent medium forms a sponge-like three-dimensional network whose pores through which the liquid crystal is arranged are more or less united with one another. Here, the expressions liquid crystal microdroplets demarcate one another, but need not be spherical at all, but may be irregularly shaped and / or deformed small liquid crystal segments. It represents.

When the optically transparent medium contains liquid crystal microdroplets, the medium is hereinafter referred to as a microdroplet matrix.
On the other hand, if there is even a slight continuous phase of the liquid crystal, this medium is described by the expression of a network structure.

[0004] NCAP (nematic curvilinear aligned)
phases, curvilinear array nematic phase) and PDLC (po
lymer dispersed liquid crystal
A film is an example of an electro-optic liquid crystal system in which liquid crystals are embedded in a matrix in the form of microdroplets. NCAP films are usually obtained by intimately mixing an encapsulated polymeric material such as polyvinyl alcohol, a liquid crystal mixture and a vehicle material such as water in a colloid mill. Thereafter, the vehicle substance is removed, for example, by drying. A suitable method is US Pat. No. 4,435,047.
It is described in. On the other hand, for example, US Pat.
8,900, Mol. Cryst, Liq. Cryst. Nonlin. Opti
c, 157 (1988) 427-441, WO 89/0
The preparation of PDLC films as described in 6264 and EP 0,272,582 involves first homogeneously mixing a liquid crystal mixture with the monomers or oligomers of the matrix-forming substance. Next, the mixture is polymerized and phase separation occurs [so-called PIPS (polymerization-i
nduced phase separation).
Furthermore, TIPS (temperature-induced phase separa)
, temperature-induced phase separation) and SIPS (solvent-induced)
phase separation, solvent-induced phase separation) [Mol. Cryst, Liq. Cryst. Inc. Nonli
n. Opt., 157 (1988) 427].

The PN (polymer network) system described in EP 0,313,053 has a sponge network structure of an optically transparent medium. The content of the liquid-crystal mixture in the light-modulating layer material is generally greater than 60%, in particular 70-90%, in such systems. PN
In order to produce a system, a mixture of a liquid crystal, a monomer or oligomer of a substance forming a three-dimensional network structure and a polymerization initiator, especially a photopolymerization initiator, is usually provided with an electrode.
After being introduced between the support plates, polymerization is performed, for example, by irradiating light.

Liquid crystals generally have a positive dielectric anisotropy Δε and a relatively high optical anisotropy. In a microdroplet matrix system, one of the indices of refraction of the liquid crystal, usually the ordinary index of refraction n _0, is selected to somewhat match the index of refraction n _M of the polymer matrix. In the case of the network structure system, there is no need to adjust the refractive index at all because the ratio of the liquid crystal normally present in the light modulation layer is very high, but this adjustment is performed to increase the light transmittance and contrast. be able to. An electrically switchable light scattering effect is seen in these electro-optical liquid crystal systems.

If no voltage is applied to the electrodes between which the microdroplet matrix or network is normally arranged in a sandwich, the light incident on the randomly arranged liquid crystal molecules is greatly scattered and the system becomes opaque. Become. When a voltage is applied, the liquid crystal molecules are aligned parallel to the electric field and perpendicular to the E vector of the transmitted light.

[0008] When microdroplet matrix systems, when a voltage is applied, light and n ₀ and n _M is incident perpendicularly to match are considered isotropic medium optically, and the system is transparent appear. Matching is necessary to prevent light scattering at the matrix / liquid crystal droplet phase interface. EP0,2
72,585, describes another embodiment in which the refractive index n _X in the liquid crystal in the case of a completely statistical orientation is aligned with the refractive index n _M of the matrix. In this case, the system is transparent in an electric field-free state, and changes to an opaque state by applying a voltage.

In the case of the network structure system, since the scattering at the network / liquid crystal phase interface is clearly not so remarkable because the ratio of the liquid crystal in the light modulating layer material is high, no refractive index matching is required at all. . When switched on, the system appears transparent even without index matching. In the case of a network structure system, it is preferable to use a liquid crystal having a high optical anisotropy in order to achieve the lowest possible transmittance without switching on.

[0010] WO 89/09807 states that in order to avoid the haze ("haze", especially "off-axis haze") often observed when the system is in the transparent state, an optically anisotropic,
For example, it has been proposed to use liquid crystalline polymer matrix materials. In this type of system, the refractive indices of the liquid crystal and the optically anisotropic matrix can be adapted to each other such that the transparent state is obtained either when a voltage is applied or when the switch is switched off.

An electro-optical liquid crystal system according to the preamble of claim 1 comprises:
In particular, it has been proposed for large area display systems, architectural applications (windows, partitions, awnings, etc.) and automobiles (windows, sunroofs, etc.). These systems are also suitable for regulating temperature by controlling the shielding of sunlight. These can be switched on by applying a DC or AC voltage.

These systems are particularly intended for "outdoor" applications and are therefore characterized by a high clearing point, a high Δε, a wide nematic range, an advantageous temperature dependence of the electro-optical parameters and a high UV and temperature stability. Liquid crystal mixture is required.

Examples of other applications include the following.

A GH display system whose spectrum ranges from a simple segment display to a display that can be applied to the desired electrode pattern using conventional printing techniques.
Applications: cars, large displays, bulletin boards, clocks.

A display with a high information content controlled by an active or passive matrix.

A projection system.

Switches.

Again, particularly high Δε, high electrical resistance,
There is a need for liquid crystal mixtures having advantageous values of electro-optic parameters and their temperature dependence, advantageous values of viscosity and high UV and temperature stability.

In microdroplet matrix systems, LC mixtures consisting of alkyl or alkoxy cyanobiphenyls and terphenyls have hitherto been customarily used. Thus, for example, US Pat. No. 4,688,900 and EP 0,272,585 describe the use of the liquid-crystal mixture E8 (from BDH, Poole, United Kingdom). This liquid crystal mixture has a high optical anisotropy Δn value of 0.247 and 54 mm
^It is characterized by a relatively high flow viscosity η value of ² / sec (20 ° C.), but at the same time has a relatively low clearing point of only 72 ° C. When a polynuclear polyphenyl compound is added to this mixture to increase the clearing point, the flow viscosity η becomes higher and the optical anisotropy Δn remains unchanged or becomes higher. High Δn values on the one hand ensure high light scattering in the opaque state, but on the other hand cause haze of the system (“haze”, in particular “off-axis haze”) when switched on, and thus a deterioration of the electro-optical properties . Indeed, in systems controlled by a relatively low frequency AC voltage, a high flow viscosity η is desirable to obtain a flicker-free display. However, on the other hand, in high information content matrix displays, liquid crystal mixtures with relatively low viscosities are necessary to achieve fast switching times.

Liquid-crystal mixtures E7 used in US Pat. No. 4,671,618, which likewise consist of alkyl and alkoxy cyanobiphenyls and terphenyls
(Made by BDH, Poole, UK) clearly has a relatively low flow viscosity of η = 39 mm ² / s and an optical anisotropy Δn of Δn = 0.225 and somewhat lower than E8, but at the same time the clearing point T _c It is quite low at 60.5 ° C. The dielectric anisotropy Δε of mixture E7 is 13.8, so Δε = 15.
6 slightly lower than E8. In order to obtain the lowest possible threshold voltage, even higher values of Δε are advantageous.

EP 0,313,053 proposes liquid-crystal mixtures based on 2- (4-cyanophenyl) pyridines for a network structure system. Liquid crystal mixtures of this kind have relatively high values for the dielectric anisotropy Δε, and thus relatively low threshold voltages and high or very high values for the optical anisotropy Δn, but at the same time these liquid crystals It is characterized by a relatively high viscosity η, a relatively low clearing point _Tc and an inadequate operating temperature range for many applications. In addition, cyanophenylpyridine compounds have particularly lower UV and temperature stability than cyanooligophenyl compounds.

The liquid crystals used so far have a wide nematic phase range, a high clearing point, a very high heat and a high nematic phase which can be optimized for the respective application and high Δε.
It satisfactorily satisfies the requirements for V stability, absence of smectic phases up to low temperatures, optical anisotropy Δn and flow viscosity η.

In addition, conventional liquid crystals often have too low a miscibility with the monomers and / or oligomers of the polymers used to form the matrix or network. This significantly impairs the production of PN systems and, in the case of microdroplet matrix systems, especially PI
It significantly limits the use of PS technology. Furthermore, these liquid crystals are often characterized by excessively high solubility in the matrix or network forming polymer. A further disadvantage of the prior liquid crystals is that, in many cases, these liquid crystals have undesired values of electro-optical parameters such as, for example, the slope of the electro-optical curve and / or electro-optical properties for the respective application, for example a threshold voltage. The purpose is to show the temperature dependence of the parameters.

Therefore, it is more suitable for specific requirements. And there is still a great need for electro-optical liquid crystal systems that do not have the above-mentioned disadvantages or only to a relatively small extent.

[0025]

SUMMARY OF THE INVENTION Accordingly, the present invention is based on the object of obtaining an electro-optical liquid crystal system and a liquid crystal which do not have the drawbacks mentioned for the prior art systems or which have only a relatively small extent. Met. Other objects of the present invention will become readily apparent to those skilled in the art from the following detailed description.

[0026]

Means for Solving the Problems Equation 1

[0027]

Embedded image (Where Q ¹ is

[0028]

Embedded image Wherein ring A ¹ and ring A ² independently of one another, are trans-1,4-cyclohexylene, 1,4-phenylene,
-Fluoro-1,4-phenylene, 3-fluoro-1,
4-phenylene and A ¹ and one of A ² , if present, are pyridine-2,5-diyl, pyrimidine-2,5-diyl, 1,3-dioxane-2,5-diyl, tetrahydro It is also pyran-2,5-diyl or naphthalene-2,6-diyl, wherein Z ¹ and Z ² are each independently a single bond, —CH ₂ CH ₂ —, —COO—, —
OCO -, - C≡C -, - CH 2 O- or is Ru two or more thereof der these bridges group, one that is present
Is -CH ₂ CH ₂ - is, Y and X is H or F independently of one another, also one of X and Y is also Cl, W is -CN, R ^1, the 1 one or alkyl having 1 to 12 C atoms which can be replaced with two non-adjacent CH ₂ groups -O- or by -CH = CH-, and m is 1 0, 1 or 2. the term) It has been found that the object of the invention can be achieved when a liquid crystal mixture containing more than one compound is used in the system.

The invention therefore comprises: a dielectrically positive liquid crystal mixture and also an optically transparent medium between two electrodes, optionally provided on a support sheet, wherein the liquid crystal molecules are switched off. One of the indices of refraction of the liquid crystal mixture essentially corresponds to the refractive index n _M of the optically isotropic transparent medium, or the index of refraction of the liquid crystal mixture is optically equal. The intrinsic refractive index of the isotropic transparent medium and / or the mass of the liquid crystal mixture divided by the mass of the optically transparent medium is greater than or equal to 1.5; Regardless, the invention relates to an electro-optical liquid crystal system which has a reduced transmission in one of the two switching states compared to the other, and wherein the liquid crystal contains one or more compounds of the formula I.

[0030]

DESCRIPTION OF THE PREFERRED EMBODIMENTS The construction of an electro-optical liquid crystal system according to the invention corresponds to the usual manner of construction of this type of system. in this case,
The term conventional mode of construction is to be interpreted broadly and includes all applications and modifications.

Therefore, for example, PDLC or NC
In the case of AP, a matrix formed by a transparent medium that finely disperses or finely encapsulates a liquid crystal mixture is disposed between conductive electrodes in a sandwich shape.

The electrodes are provided in particular on a support sheet, for example of glass, plastic or the like. However, if desired, the electrodes can be provided directly on the matrix and the use of a support can be omitted.

In the case of the network system, the liquid crystal is placed in the pores of a sponge-like three-dimensional network, or an optically transparent medium is placed in the liquid crystal in the form of small, for example, spherical particles. The network structure is usually arranged between supports provided with electrodes to prevent liquid crystal from escaping.

Since both the network system and the microdroplet matrix system can function reflectively or transmissively, at least one electrode and, if present, its associated support are transparent. Both systems usually do not include a polarizer. The result is a distinctly higher transmission.
Furthermore, no orientation phase is required. This is a considerable technical simplification in the production of these systems compared to conventional liquid crystal systems such as, for example, TN or STN cells.

The microdroplet matrix or three-dimensional network is based in particular on isotropic thermoplastics, thermosets and elastomers. Depending on the intended use, the resulting system can be flexible, elastic or rigid.

Systems based on thermoplastic polymers can easily be deformed by the action of mechanical stress at temperatures above the glass temperature of the matrix. This can be used, for example, in a microdroplet matrix system to solidify the drops into a particular deformed shape by cooling the matrix to a temperature below the glass temperature. further,
For example, the matrix can be mechanically stretched at a temperature above the glass temperature or oriented by the action of an electric or magnetic field. This orientation is carried out at a temperature below the glass temperature, making the matrix optically anisotropic.

The plastic and / or elastic system is preferably based on thermoplastics and / or elastomers, but it is preferable to use thermosetting resins for producing rigid systems. These can be mechanically deformed, for example, during curing, so that, for example, the shape and arrangement of the microdroplets is constant in the cured matrix.

Materials which are particularly suitable for producing microdroplet matrices or networks are well-documented in the literature. For example, US 4,435,047 or Liquid
Liquid Crystals, 3 , (1988)
1543 proposes, for example, water-soluble polymers such as polyvinyl alcohol PVA or latex emulsions. On the other hand, US 4,672,618, US 4,
673, 255, US 4,688,900, WO 85 /
04262 and Mol. Cryst. Liq. Cryst. Inc. Nonli
In Opt., 157 (1988) 427, synthetic resins, such as, for example, epoxy resins and polyurethanes, which are thermally cured, are listed as suitable matrix materials. EP 0,272,585 describes matrix or network materials based on photocurable vinyl compounds, and WO 89/06264 proposes the copolymerization of polyfunctional acrylates containing polyfunctional mercaptans. Other details of polymers particularly suitable for matrix systems are described, for example, in EP 0,165,063, EP 0,
345,029, EP0,357,234 or EP
0,205,261.

Regarding the network system, many three-dimensional crosslinkable monomers such as, for example, di- and triacrylates
0,313,053.

However, further transparent substances such as inorganic oxide glass bodies (US Pat. No. 4,814,211) and other inorganic substances (for example, JP-A-63-303)
325) or alternatively other materials can be used for the microdroplet matrix and network system.

The above materials are merely illustrative of the invention and do not limit the invention in any way. In principle, all transparent substances which make it possible to produce the abovementioned microdroplet matrices or networks according to the preamble of claim 1 can be used.

Preferred embodiments of the electro-optical liquid crystal system according to the present invention are NCAP films, PDLC films and microdroplet matrix systems produced by an improved method. Methods for producing these films are described, for example, in US
4,688,900, US4,673,255, US
4,671,618, WO85 / 0426, US4,4
35,047, EP 0,272,595, Mol. Cry
St. Liq. Cryst. Inc. Nonlin. Opt., 157 (198
8) 427, Liquid Crystals, 3 , (198
8) 1543, EP0,165,063, EP0,34
5,029, EP0,357,234 and EP0,2
05,261.

A further preferred embodiment of the electro-optical liquid crystal system according to the invention is a network system whose manufacture is described in EP 0,313,053. In the present invention, arrangements in which transparent media are individually dispersed in liquid crystals, for example, in the form of spherical particles, as described in GB 1,442,360, also belong to the network system.

However, embodiments in which the transparent medium has an intermediate structure between the network structure on the one hand and the microdroplet matrix structure on the other hand are also included in the present invention.

Further, other embodiments not specifically described herein are also included in the present invention.

The thickness d of the electro-optical system is usually chosen to be as small as possible to achieve the lowest possible threshold voltage V _th . Thus, layer thicknesses of 0.8 mm and 1.6 mm have been reported, for example, in US Pat. No. 4,435,047, with values between 10 μm and 300 μm being considered in US Pat.
00 and values from 5 μm to 30 μm are EP 0,313,
This is shown as layer thickness at 053. Only in exceptional cases, the electro-optical system according to the invention has a layer thickness d significantly greater than a few mm, but preferably the layer thickness is d ≦ 2 mm.

The threshold voltage is also affected by the size of the microdroplets or the mesh width of the mesh structure. In general, a relatively small microdroplet results in a relatively high threshold voltage V _th but with a shorter switching time t _on or t _off (US Pat. No. 4,673,255). Experimental methods that affect average droplet size are described, for example, in US Pat. L. Mol. Cryst. Liq. Cryst. In West
Inc. Nonlin. Opt., 157 (1988) 427. US 4,673,255 is 0.1 μm to 8
Although an average droplet diameter of μm is indicated, for example, a matrix consisting of a glass body has pores with a diameter of 15 to 2,000 °. With respect to the mesh width of the PN-based network structure, the preferable range of 0.5 μm to 2 μm is EP0,31.
3,053.

However, an essential difference between the electro-optical liquid crystal system of the present invention and the conventional conventional one is that a different liquid crystal mixture is used.

The liquid-crystal mixtures according to the invention comprise at least one compound of the formula I
Contains species of compounds.

The compounds of the formula I are of the sub-formula I2, I3 and I
4:

[0051]

Embedded image 2, 3, and 4 cyclically dielectrically positive or dielectrically neutral compounds.

In the compounds of the formulas I2 to I4, X and Y are, independently of one another, H, F or Cl, in particular H
Or F. The compounds of the formulas I3 and I4 preferably contain no more than two, in particular no more than one heterocycle.
In the compounds of the formulas I3 and I4, one of the bridges Z ¹ and Z ² is preferably a single bond.

In the compounds of the formula I and of the sub-formulae of the compounds I2 to I4, R ¹ is 1 to 12 of which one or two non-adjacent CH ₂ can also be replaced by —O— or —CH ＝ CH—. Alkyl having a C atom of

If R ¹ is an alkyl and / or alkoxy group, it can be straight-chain or branched. This group is straight-chain and preferably has 1, 2, 3, 4, 5, 6 or 7 C atoms and is thus methyl, ethyl, propyl, butyl, pentyl, hexyl,
Preferably it is heptyl, methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy or heptoxy, furthermore octyl, nonyl, decyl, undecyl, dodecyl, octoxy, nonyloxy, decyloxy, undecyloxy or dodecyloxy.

Oxaalkyl is straight-chain 2-oxapropyl (= methoxymethyl), 2-oxabutyl (= ethoxymethyl) or 3-oxabutyl (= 2-methoxyethyl), 2-, 3- or 4-oxapentyl,
-, 3-, 4- or 5-oxahexyl, 2-3
-, 4-, 5- or 6-oxaheptyl, 2-3
-, 4-, 5-, 6- or 7-oxaoctyl, 2
-, 3-, 4-, 5-, 6-, 7- or 8-oxanonyl, or 2-, 3-, 4-, 5-, 6-, 7-,
Preferably it is 8- or 9-oxadecyl.

If R ¹ is an alkyl group in which one CH ₂ group has been replaced by —CH ＝ CH—, this can be straight-chain or branched. This group is straight-chain and 2
Those having from 10 to 10 C atoms are preferred. Thus, this group is especially vinyl, 1- or 2-propenyl, 1-, 2- or 3-butenyl, 1-, 2-, 3- or 4-pentenyl, 1-, 2-, 3-, 4- or 5-hexenyl, 1-, 2-, 3-, 4-, 5- or 6-heptenyl, 1-, 2-, 3-, 4-, 5-, 6- or 7-octenyl, 1-, 2- , 3-, 4-, 5-,
6-, 7- or 8-nonenyl, or 1-, 2-, 3-
-, 4-, 5-, 6-, 7-, 8- or 9-decenyl.

In the compounds of the formula I, the radical R ¹ can be straight-chain or branched, but is preferably straight-chain. The compound of formula I with a branched alkyl or alkoxy group also has better solubility in common liquid-crystal substrates, and is important in some cases, but if it is optically active, , Especially as a chiral dopant. An electro-optical system according to the preamble of claim 1 wherein the liquid crystal contains one or more chiral components is described in DE 39 11 255.1.

Branching groups of this kind generally contain one or less chain branches. Preferred branching groups are isopropyl, 2-
Butyl (= 1-methylpropyl), isobutyl (= 2-
Methylpropyl), 2-methylbutyl, isopentyl (= 3-methylbutyl), 2-methylpentyl, 3-methylpentyl, 2-ethylhexyl, 2-propylpentyl, 2-octyl, isopropoxy, 2-methylpropoxy, 2-methyl Butoxy, 3-methylbutoxy, 2
-Methylpentoxy, 3-methylpentoxy, 2-ethylhexoxy, 2-methylhexoxy, 2-octyloxy, 2-oxa-3-methylbutyl, 3-oxa-4
-Methylpentyl, 4-methylhexyl, 2-nonyl,
6-methyloctoxy, 2-methyl-3-oxapentyl and 2-methyl-3-oxahexyl.

The compounds of the formula I are described in the literature [eg Houben-Weyl, published by Georg-Thieme publisher, Stuttgart, "Methoden der Organischen Chemie". , Vo
l. IX, p. And a reaction method suitable for the above-mentioned reaction, particularly in accordance with a known method. In this regard, it is also possible to use alternatives which are known per se, but which are not explained here in further detail.

Particular preference is given to a small group of compounds of the subformula Ia.

[0061]

Embedded image (Wherein ring A ³ and ring A ⁴ are independently 1,4-
Cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene or 3-fluoro-1,4-phenylene, and R ¹ has the meaning of claim 1;
X ¹ is H or F, and the following number combination 1
５5 applies to n, Z ³ and Z ⁴ :

[0062]

[Table 2]

For simplicity, in the following, Cyc is trans-1,4-cyclohexylene, Phe is 1,4-phenylene and Phe. 2F is 2-fluoro-1,4-phenylene; Phe. 3F is 3-fluoro-1,4-phenylene; Phe. F2 is 2,3-difluoro-1,4-phenylene;
e. 3F5F is 3,5-difluoro-1,4-phenylene; Phe. F is 2- or 3-difluoro-
1,4-phenylene, and Pyr is pyrimidine-2,
5-diyl, Pyd is pyridine-2,5-diyl, Dio is 1,3-dioxane-2,5-diyl, and Thp is tetrahydrofuran-2,5-diyl.
This is Jiyl. Acronyms Pyr, Pyd, Dio and T
hp include in each case the two possible positional isomers and the acronym Phe. 2Cl, Phe. 3C
1, Phe. 3Cl5Cl and Phe. The meaning of Cl is clear from the meaning of the individual fluorinated 1,4-phenylene groups.

Compounds of sub-formula Ia have the following sub-formula Ia
Compounds of 2-1 to 1a2-6 include preferred bicyclic compounds.

R ¹ -Phe-Phe.3F-CN Ia2-1 R ¹ -Phe-Phe.3F5F-CN Ia2-2 R ¹ -Cyc-CH ₂ CH ₂ -Phe.3F-CN Ia2-3 R ^1- Cyc-CH ₂ CH ₂ -Phe.3F5F-CN Ia2-4 R ¹ -Cyc-Phe.3F-CN Ia2-5 R ¹ -Cyc-Phe.3F5F-CN Ia2-6

In the compounds of the subformulas Ia2-1 to Ia2-6, R ¹ has the meaning given for the compounds of the formula I. R ¹ is preferably alkyl, alkenyl or alkoxy having ¹ to 10, especially 1 to 8, C atoms. More preferred are n-alkoxyalkyl compounds, especially n-methoxyalkyl, n-alkoxyethyl and n-alkoxymethyl compounds. Formula Ia2-2, Ia2
Liquid crystal media containing the compounds -4 and Ia2-6 have particularly advantageous values for the dielectric anisotropy. Lower formula Ia2
In the compounds of -1 and Ia2-2, Phe may be laterally fluorinated independently of one another in each case.

Compounds of sub-formula Ia have the following sub-formula Ia
3-1 to Ia3-16, and preferably includes tricyclic compounds.

R ¹ -Cyc-Phe-CH ₂ CH ₂ -Phe.3F-CN Ia3-1 R ¹ -Cyc-Phe-CH ₂ CH ₂ -Phe.3F5F-CN Ia3-2 R ¹ -Cyc-Cyc- CH ₂ CH ₂ -Phe.3F-CN Ia3-3 R ¹ -Cyc-Cyc-CH ₂ CH ₂ -Phe.3F5F-CN Ia3-4 R ¹ -Cyc-CH ₂ CH ₂ -Phe-Phe.3F-CN Ia3-5 R ¹ -Cyc-CH ₂ CH ₂ -Phe-Phe.3F5F-CN Ia3-6 R ¹ -Cyc-CH ₂ CH ₂ -Cyc-Phe.3F-CN Ia3-7 R ¹ -Cyc-CH ₂ CH ₂ -Cyc-Phe.3F5F-CN Ia3-8 R ¹ -Phe-Phe-Phe.3F-CN Ia3-9 R ¹ -Phe-Phe-Phe.3F5F-CN Ia3-10 R ¹ -Cyc-Phe- Phe.3F-CN Ia3-11 R ¹ -Cyc-Phe-Phe.3F5F-CN Ia3-12 R ¹ -Cyc-Cyc-Phe.3F-CN Ia3-13 R ¹ -Cyc-Cyc-Phe.3F5F-CN Ia3-14 R ¹ -Phe-CH ₂ CH ₂ -Phe-Phe.3F-CN Ia3-15 R ¹ -Phe-CH ₂ CH ₂ -Phe.3F5F-CN Ia3-16 R ¹ -Phe-Phe-CH ₂ CH ₂ -Phe.3F-CN Ia3-17 R ¹ -Phe-Phe-CH ₂ CH ₂ -Phe.3F5F-CN Ia3-18

In the compounds of the subformulae Ia3-1 to Ia3-18, R ¹ has the meaning given for the compounds of the formula I, R ¹ is an n-alkyl having ¹ to 10 C atoms, n
-Alkenyl or n-alkoxy, and also n-alkoxymethyl or n-alkoxyethyl having 1 to 18 C atoms.

R ¹ is methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, methoxymethyl, ethoxymethyl, propoxymethyl, butoxymethyl, pentoxymethyl, Formula Ia3-1 which is methoxyethyl, ethoxyethyl, propoxyethyl, butoxyethyl or pentoxyethyl
The compound of Ia3-18 is a particularly preferred compound.

In the compounds of the subformulae Ia3-1 to Ia3-18, the Phe groups may in each case independently of one another be laterally fluorinated, in particular monofluorinated.

Formulas Ia, Ia2-1 to Ia2-6 and I
Most of the compounds a3-1 to Ia3-18 are known, and preferably DE3,209,178, JP62
−103,057, DE3,929,418, JP63
-216,858, DE3,401,320, EP0,
119,756, DE3,632,411, EP0,2
05,998, in particular DE 3,929,
418.

Formula Ia, specifically Formulas Ia2-1 to Ia2-
Liquid crystal mixtures containing the compounds of formulas 6 and Ia3-1 to Ia3-18 are particularly suitable for use in the electro-optical system according to the invention, and also have advantageous values for the birefringence Δn and the flow viscosity η, high stability It is characterized by low miscibility with the polymers used for the matrix, and particularly advantageous values for the wide mesogenic range, relatively high clearing points and dielectric anisotropy, the threshold voltage and the temperature dependence of the electro-optical parameters.

The liquid crystals used in the electro-optical liquid crystal system according to the invention have a sub-formula Ia of 1 to 40%, in particular 5 to 30%, in particular sub-formulae Ia2-1 to Ia2-6 and Ia3-1 to Ia3-.
Preferably, it contains 18 compounds. These liquid crystals have 1 to 5, in particular 1 to 3, lower formulas Ia, in particular lower formulas Ia2-1 to Ia2-6 and Ia3-1 to Ia3-.
Preferably, it contains 18 compounds.

The liquid-crystal mixtures are particularly preferably based on the compounds of the following formulas II to IV in addition to the compounds of the lower formula Ia.

TW ¹ -Phe-CN II RW ¹ -Cyc-CN III TV-Phe-CN IV (wherein R in each case, independently of one another, one or two non-adjacent CH ₂ groups To -O-, -CO
An alkyl group having 1 to 15 C atoms, which can also be replaced by-and / or -CH = CH-,
. ¹ is Phe (F) -Y ¹ or Cyc-Y ^1, Y ¹ is a single bond, a -COO- or -OCO-, V is pyridine-1,5-diyl or pyrimidine -
2,5-diyl, and T is R, R-Phe. (F)-
Y ¹ or R-Cyc-Y ¹ , and Ph
e. (F) is 1,4-phenylene, 2-fluoro-1,
4-phenylene or 3-fluoro-1,4-phenylene). In the compounds of the formulas II to IV, the terminal group Phe
-CN, particularly when Y ¹ is a -COO- or -OCO-, may be mono- or di-fluorinated 3 and / or 5 site by F.

The compounds of the formulas II to IV are known or described in the literature [eg Hoven-Weyl, "Methods of Organic Chemistry", published by Georg-Sime, Stuttgart, V.
ol. IX, p. 867 et seq.], And under any known reaction conditions suitable for the above reaction. In this regard, it is also possible to use alternatives which are known per se, but which are not explained here in further detail.

The lower formulas Ia, in particular the lower formulas Ia2-1 to Ia2, in the liquid-crystal mixtures used in the electro-optical liquid-crystal systems according to the invention.
-6 and one or more compounds selected from the group of compounds of Ia3-1 to Ia3-16 and one or more compounds selected from the group of compounds of formulas II to IV, the content of the component mixture is 15 % To 100%, preferably 25% to 100%. Sub-formula Ia, especially sub-formula Ia2-1
In addition to one or more compounds Ia2-6 and Ia3-1 to Ia3-16, this component mixture comprises the following compound II1
It is particularly preferred that it comprises one or more compounds selected from the subgroups of -II25, III1-III3 and IV1-IV8.

R-Cyc-Phe-CN II1 R-Cyc-COO-Phe-CN II2 R-Cyc-COO-Phe.3F-CN II3 R-Cyc-COO-Phe.3F5F-CN II4 R-Phe-Phe -CN II5 R-Phe-COO-Phe-CN II6 R-Phe-COO-Phe.3F-CN II7 R-Phe-COO-Phe.3F5F-CN II8 R-Cyc-Phe-Phe-CN II9 R-Cyc -COO-Phe-Phe-CN II10 R-Cyc-Phe-COO-Phe-CN II11 R-Cyc-COO-Phe-Phe.3F-CN II12 R-Cyc-COO-Phe-Phe.3F5F-CN II13 R -Cyc-Phe-COO-Phe.3F-CN II14 R-Cyc-Phe-COO-Phe.3F5F-CN II15 R-Phe-Phe-Phe-CN II16 R-Phe-Phe.3F-Phe-CN II17 R -Phe-Phe.2F-Phe-CN II18 R-Phe-COO-Phe-Phe-CN II19 R-Phe-COO-Phe-Phe.3F-CN II20 R-Phe-COO-Phe-Phe.3F5F-CN II21 R-Phe-Phe-COO-Phe-CN II22 R-Phe-Phe-COO-Phe.3F-CN II23 R-Phe-Phe-COO-Phe.3F5F-CN II24 R-Cyc-Cyc-CN III1 R -Cyc-COO-Cyc-CN III2 R-Cyc-OCO-Cyc-CN III3 R-Pyd-Phe-CN IV1 R-Pyr-Phe-CN IV2 R-Pyd-Phe-Phe-CN IV3 R-Pyr-Phe -Phe-CN IV4 R-Phe-Pyd-Phe-CN IV5 R-Phe-Pyr-Phe-CN IV6 R-Cyc-Pyr-Phe-CN IV7 R-Cyc-Pyd-Phe-CN IV8

The lower formulas Ia, especially the lower formulas Ia2-1 to Ia
2-6 and at least one compound selected from the compounds of Ia3-1 to Ia3-16,
One or more compounds selected from the compounds of II24 and at least one compound selected from the compounds of the subformulas IV1 to IV8
Component mixtures containing certain compounds are very particularly preferred.

Preference is given to liquid-crystal mixtures based on the following component mixtures T (Ia) 1-4, each containing at least one compound from the compounds of the formulas mentioned in each case. The following table further shows the preferred masses of these compounds in the component mixture. The component mixture is 2 to 38 types,
It preferably contains 2 to 35, especially 2 to 25 compounds. The sum of the masses of these compounds in the component mixture is 100%. The mass of the component mixture in the liquid crystals according to the invention is between 10% and 100%, in particular between 15% and 100%, more particularly between 25% and 100%.

[0082]

[Table 3]

It is also particularly preferred for the system according to the invention that the liquid-crystal mixtures are based on the following compounds:

R-Cyc-Phe-CN II1 R-Phe-Phe-CN II5 R-Cyc-Phe-Phe-CN II9 R-Phe-Phe-Phe-Phe-CN II16

This system is characterized in that the liquid crystal mixture contains 5 to 60% of one or more compounds of the following formula in order to increase the dielectric anisotropy.

R-Phe.2F-Phe-CN II25 R-Phe.3F-Phe-CN II25a R ¹ -Phe-Phe.3F-CN Ia2-1 R ¹ -Phe-Phe-Phe.3F-CN Ia3- 9 R-Phe-Phe.2F-Phe-CN II18 R-Phe-Phe.3F-Phe-CN II17 R-Cyc-Phe.2F-Phe-CN II26 R-Cyc-Phe.3F-Phe-CN II27 R -Phe.F-Phe.F-Phe-CN II28 (wherein, the meanings of R ¹ and R are as described above, and R is preferably an alkyl group having 2 to 7 C atoms. Preference is given to mixtures of this type and are also a subject of the present invention.

In the following, this liquid crystal mixture component based on the compounds II1, II5, II9 and II16 is sometimes referred to as component (i), while the compounds II25, Ia2-
1, Ia3-9, II17, II18, II26, II27, II
Components based on 28 and II25a are sometimes referred to as component (ii). These liquid crystal mixtures may consist only of components (i) and (ii), but it is also possible for the liquid crystal mixture to contain other components (iii) and (iv). Component (iii) is selected such that the birefringence Δn and / or the ordinary refractive index n ₀ and / or other refractive indices and / or other parameters of the liquid crystal are specifically optimized for the respective application. Other nematic or nematic forming substances. Nematic or nematic forming substances which can also be preferably used for component (iii) are further listed below. Component (iv) comprises, for example, chiral dopants for reducing the cholesteric phase and / or polychromatic dyes and / or other additives for modifying other properties of the liquid crystal mixture, for example, conductivity. I have. In this regard, compounds of component (iv) can be both mesophase-forming and non-mesophase-forming.

The mass of the component (i) in the liquid crystal is 10 to 80.
%, Especially 15-70%, more particularly 15-65%. If the liquid crystal mixture is to have a high birefringence of Δn> 0.24, component (i) may comprise 4-alkyl and / or 4-alkoxy-4′-cyanocobiphenyls and / or 4-alkyl and / or 4-alkoxy-4 "-cyanoterphenyls and / or
Or 4- (trans-4-alkyl or trans-
4-alkoxycyclohexyl) -4′-cyanobiphenyls. On the other hand, the liquid crystal mixture
When having a birefringence of 3 ≦ Δn ≦ 0.22,
Component (i) preferably contains 4- (trans-4-alkyl or trans-4-alkoxycyclohexyl) benzonitrile in addition to one or more of the high Δn compounds of component (i) just described. .

Preferred formulas II25, II25a and Ia2
-1 in laterally fluorinated biphenyls,
R ¹ is methyl, ethyl, propyl, butyl, pentyl,
Preference is given to hexyl, heptyl, methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy and heptoxy.

Further, the component (ii) has the formula Ia3-9, II1
It is preferred to include laterally monofluorinated tricyclic compounds of 7, II18, II26 and II27. In these compounds, R ¹ is 1 to 7 C atoms, in particular 2
Preference is given to alkyl, alkoxy or alkoxyalkyl having ７7 C atoms, in particular 2 to 5 C atoms.

If a liquid crystal mixture having a high clearing point is to be obtained, component (i) preferably comprises tricyclic compounds of the formulas II9 and II16 and / or
I) has the formula Ia3-9, II17, II18, II26, II27
And II28 tricyclic compounds. Liquid-crystal mixtures comprising at least one compound of the formulas II9 and II16 and at least one compound of the formulas Ia3-9, II17, II18 and II26-28 show that these mixtures generally have relatively high or high values for Δε. And a high clearing point.

The liquid-crystal mixture containing components (i) and (ii) should have a clearing point of T _c > 75 ° C., especially T _c > 80 ° C., and more particularly T _c > 85 ° C. preferable.

Formulas II25, II25a, Ia2-1 and Ia3
Laterally fluorinated compounds of -9, II18, II17 and II26-28 usually have very good solubility in component (i) and the modified mixture. Formulas Ia3-9, II18, II17 and II26-28 in liquid crystal mixtures
The solubility of the laterally fluorinated terphenyls is generally substantially better than the solubility of the non-fluorinated terphenyl of formula II16.

One or more of the formulas II25, II25a, Ia2-
1, Ia3-9, II18, II17 and II26-28,
In particular, formulas Ia2-1, Ia3-9, II18, II17, II2
5, liquid crystals mixtures containing laterally fluorinated compounds II 25a and II 26-27 are characterized by better UV and temperature stability than the mixtures E7 and E8 known from the prior art, or also the corresponding mixtures. .

Liquid-crystal mixtures which also contain components (i) and (ii) and, if desired, other components (iii) and (iv), and electro-optical systems containing these have advantageous properties. In particular, these mixtures have high or relatively high dielectric anisotropy and / or high or relatively high birefringence.
Or it has a high clearing point. Formulas II1, II5, II9,
II16, II25, II25a, Ia2-1, Ia3-9,
The compounds II18, II17, II26, II27 and II28 are sufficiently stable to heat and radiation energy for most applications and very stable to chemicals. Liquid-crystal mixtures containing these compounds are very nematic, especially even at low temperatures, and have advantageous values for η. Electro-optical systems operated with these mixtures have advantageous values for the electro-optical parameters and their temperature dependence, high contrast and low angle dependence of the contrast and also good manufacturability.

Those liquid crystal mixtures are represented by the lower formula Ib

[0097]

Embedded image [Where Q ² is

[0098]

Embedded image And one of ring A ⁵ and ring A ⁶ is

[0099]

Embedded image (Where V ¹ is N or CH) and the other, if present, is trans-1,4-cyclohexylene or 1,4-phenylene, X ² and Y ²
Are independently H or F, and P is 0 or 1
And Z ⁵ and Z ⁶ are, independently of one another, a single bond or CH ₂ CH ₂ , and R ¹ has the meaning given in the claims]. Further preferred is an electro-optical liquid crystal system according to the invention comprising the compound

Particularly preferred liquid crystal mixtures are X ² or Y ²
A compound of subformula Ib, wherein at least one of F is F

[0101]

Embedded image Is a mixture containing at least one of the following.

Compounds of the subformula IbF are of the formula IbF2
-1 to IbF2-8 include bicyclic compounds which are monofluorinated laterally or difluorinated laterally.

R ¹ -Pyd-Phe.3F-CN IbF2-1 R ¹ -Pyd-Phe.3F5F-CN IbF2-2 R ¹ -Pyr-Phe.3F-CN IbF2-3 R ¹ -Pyr-Phe.3F5F -CN IbF2-4 R ¹ -Pyd-CH ₂ CH ₂ -Phe.3F-CN IbF2-5 R ¹ -Pyd-CH ₂ CH ₂ -Phe.3F5F-CN IbF2-6 R ¹ -Pyr-CH ₂ CH ₂ -Phe.3F-CN IbF2-7 R ¹ -Pyr-CH ₂ CH ₂ -Phe.3F5F-CN IbF2-8

In the compounds of the formulas IbF2-1 to IbF2-8, R ¹ is preferably alkyl or alkoxy having ¹ to 10, in particular 1 to 8 C atoms, more preferably n-alkoxyalkyl, especially n-alkoxy. They are also alkoxymethyl and n-alkoxyethyl. Formula IbF2-4 having a 3,5-difluoro-4-cyanophenyl group,
IbF2-4, IbF2-6 and / or IbF2-
Liquid crystals containing the compound of No. 8 have particularly advantageous values for the dielectric anisotropy. R ¹ is methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-
Heptyl, n-octyl, n-nonyl, n-decyl, n
Formula IbF2-1 to IbF2 which is -methoxy, n-ethoxy, n-propoxy, n-butoxy, n-pentoxy, n-hexoxy, n-heptoxy, n-octoxy, n-nonoxy, n-decoxy or n-undecoxy −
Compound 8 is a very highly preferred compound.

The compounds of the formula IbF can be prepared from the following laterally mono- or difluorinated compounds of the formulas IbF3-1 to IbF3-36:
Further preferred is a tricyclic compound.

R ¹ -Pyd-Phe-Phe.3F-CN IbF3-1 R ¹ -Pyr-Phe-Phe.3F-CN IbF3-2 R ¹ -Pyd-Phe-Phe.3F5F-CN IbF3-3 R ¹ -Pyr-Phe-Phe.3F5F-CN IbF3-4 R ¹ -Phe-Pyd-Phe.3F-CN IbF3-5 R ¹ -Phe-Pyd-Phe.3F5F-CN IbF3-6 R ¹ -Phe-Pyr- Phe.3F-CN IbF3-7 R ¹ -Phe-Pyr-Phe.3F5F-CN IbF3-8 R ¹ -Cyc-Pyd-Phe.3F-CN IbF3-9 R ¹ -Cyc-Pyd-Phe.3F5F-CN IbF3-10 R ¹ -Cyc-Pyr-Phe.3F-CN IbF3-11 R ¹ -Cyc-Pyr-Phe.3F5F-CN IbF3-12 R ¹ -Pyd-Phe-CH ₂ CH ₂ -Phe.3F-CN IbF3-13 R ¹ -Pyd-Phe-CH ₂ CH ₂ -Phe.3F5F-CN IbF3-14 R ¹ -Pyr-Phe-CH ₂ CH ₂ -Phe.3F-CN IbF3-15 R ¹ -Pyr-Phe- CH ₂ CH ₂ -Phe.3F5F-CN IbF3-16 R ¹ -Phe-Pyd-CH ₂ CH ₂ -Phe.3F-CN IbF3-17 R ¹ -Phe-Pyd-CH ₂ CH ₂ -Phe.3F5F-CN IbF3-18 R ¹ -Phe-Pyr-CH ₂ CH ₂ -Phe.3F-CN IbF3-19 R ¹ -Phe-Pyr-CH ₂ CH ₂ -Phe.3F5F-CN IbF3-20 R ¹ -Cyc-Pyd- CH ₂ CH ₂ -Phe.3F-CN IbF3-21 R ¹ -Cyc-Pyd-CH ₂ CH ₂ -Phe.3F5F-CN IbF3-22 R ¹ -Cyc-Pyr-CH ₂ CH ₂ -Phe.3F-CN IbF3-23 R ¹ -Cyc-Pyr-CH ₂ CH ₂ -Phe.3F5F-CN IbF3-24 R ¹ -Pyd-CH ₂ CH ₂ -Phe-Phe.3F-CN IbF3-25 R ¹ -Pyd-CH ₂ CH ₂ -Phe-Phe.3F5F-CN IbF3-26 R ¹ -Pyr-CH ₂ CH ₂ -P he-Phe.3F-CN IbF3-27 R ¹ -Pyr-CH ₂ CH ₂ -Phe-Phe.3F5F-CN IbF3-28 R ¹ -Phe-CH ₂ CH ₂ -Pyd -Phe.3F-CN IbF3-29 R ¹ -Phe-CH ₂ CH ₂ -Pyd-Phe.3F5F-CN IbF3-30 R ¹ -Phe-CH ₂ CH ₂ -Pyr-Phe.3F-CN IbF3-31 R ¹ -Phe-CH ₂ CH ₂ -Pyr-Phe.3F5F-CN IbF3-32 R ¹ -Cyc-CH ₂ CH ₂ -Pyd-Phe.3F-CN IbF3-33 R ¹ -Cyc-CH ₂ CH ₂ -Pyd -Phe.3F5F-CN IbF3-34 R ¹ -Cyc-CH ₂ CH ₂ -Pyr-Phe.3F IbF3-35 R ¹ -Cyc-CH ₂ CH ₂ -Pyr-Phe.3F5F IbF3-36

In the compounds of the formulas IbF3-1 to IbF3-36, R ¹ is preferably n-alkyl or n-alkoxy having ¹ to 10 C atoms, more preferably having 1 to 8 C atoms. It is also n-alkoxymethyl or n-alkoxyethyl. Preferred Formula IbF3-
Compounds 1 to IbF3-36 have high or relatively high values for the dielectric anisotropy Δε. In this case, the structural element

[0108]

Embedded image Formulas IbF3-6, IbF3-8, IbF3 containing
-9, IbF3-12, IbF3-30, IbF3-3
2, The difluorinated compounds of IbF3-34 and IbF3-36 are characterized by particularly very high values for Δε.

The compound of the formula IbF is described in DE 3,209,17
8, DE 4,002,609, DE 4,001,02
2, DE4,012,014, DE4,012,023
And 3,315,295.

Formula IbF, especially Formulas IbF2-1 to IbF2
-8 and liquid crystal mixtures containing one or more compounds of IbF3-1 to IbF3-36 and electro-optical systems filled with these liquid crystal mixtures have advantageous values for birefringence Δn and flow viscosity η, high stability, It is characterized by low miscibility with the polymers used for the matrix, a wide mesogenic range, a relatively high clearing point and especially advantageous values for the dielectric anisotropy, the threshold voltage and the temperature dependence of the electro-optical parameters.

These liquid crystal mixtures have a content of 1 to 40%, especially 5%.
３０30% of the formula IbF, in particular the formulas IbF2-1 to IbF2-
8 and IbF3-1 to IbF3-36. In this case, the liquid crystal mixture is 1 to 5
Species, in particular 1 to 3, of the formulas IbF, in particular formulas IbF2-1 to IbF
It preferably contains the compounds bF2-8 and IbF3-1 to IbF3-36.

Formula IbF, especially IbF2-1 to IbF2-
8 and one or more compounds selected from the group of compounds IbF3-1 to IbF3-36, and further compounds II1 to II2
8, a liquid crystal mixture containing at least one compound selected from the group consisting of III-III3 and IV1-IV8 is particularly preferred. Formulas IbF, especially formulas IbF2-1 to IbF2-8 and IbF3-1 to Ib, in the liquid-crystal mixtures according to the invention
F3-36 and at least one compound of the formula II1-
The component mixture comprising at least one compound of II28, III1 to III3 and IV1 to IV8 has a mass of 15% to 100%,
In particular, it is preferably from 25% to 100%. Formula IbF,
In particular, the formulas IbF2-1 to IbF2-8 and IbF3-1
At least one compound selected from the group consisting of
Very particular preference is given to component mixtures T (IbF) 1 to T (IbF) 8 which contain, in addition to the species compounds, at least one compound selected from the group of compounds indicated in each case.

[0113]

[Table 4]

Preference is given to liquid-crystal mixtures based on the following component mixtures T (IbF) 9 to 13, each containing at least one compound from the compounds of the formulas mentioned in each case. The following table further shows the preferred masses of these compounds in the component mixture. The component mixture is 2-38
Species, preferably from 2 to 35, in particular from 2 to 25 compounds. The sum of the masses of these compounds in the component mixture is 100%. The mass of the component mixture in the liquid crystals according to the invention is between 10% and 100%, in particular between 15% and 100%, more particularly between 25% and 100%.

[0115]

[Table 5] Compounds of the formula Ib, wherein the terminal group -Phe-CN is not fluorinated

[0116]

Embedded image And a liquid crystal mixture containing at least one of the following.

These compounds of the subformula IbN have the following formula
Including bicyclic compounds of IV1 to IV2 and IbN2-1 to IbN2-2.

R ¹ -Pyd-Phe-CN IV1 R ¹ -Pyr-Phe-CN IV2 R ¹ -Pyd-CH ₂ CH ₂ -Phe-CN IbN2-1 R ¹ -Pyr-CH ₂ CH ₂ -Phe-CN IbN2-2

Formulas IV1 to IV2 and IbN2-1 to IbN
R ¹ of compound 2-2 is an alkyl or alkoxy having ¹ to 10, especially 1 to 8, C atoms. More preferred are n-alkoxyalkyl compounds, especially n-alkoxymethyl and n-alkoxyethyl compounds.

Compounds wherein R ¹ is methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, hexoxy or octoxy are of the formulas IV1 to IV2 and IbN2-1 to IbN
bN2-2 is a very particularly preferred compound. Formula IV1
Of the formulas IV2 and IbN2, in particular of the formulas IV2 and Ib
The compound of N2-2 has a high or relatively high value for the dielectric anisotropy Δε. The liquid crystal medium of the present invention is a compound
Which compound of IV1 to IV2 and IbN2-1 to IbN2-2 is preferably contained mainly depends on the intended use of the electro-optical system of the present invention. Thus, for example, the compounds of the formulas IV1 and IV2 have a relatively high clearing point, in particular a relatively high optical anisotropy, while the compounds of the formula IbN2
The compounds -1 and IbN2-2 are characterized, for example, by relatively low flow viscosities.

Liquid crystal mixtures containing compounds of the formulas IV1 and / or IV2 are particularly preferred for matrix systems, but are less suitable for network systems. On the other hand, compounds IbN2-1 to IbN2-2 are generally particularly preferred as a mixture component of a matrix and a network structure.

Compounds of formula IbN further include the following tricyclic compounds of formulas IV3 to IV8 and IbN3-1 to IbN3-18.

R ¹ -Pyd-Phe-Phe-CN IV3 R ¹ -Pyr-Phe-Phe-CN IV4 R ¹ -Pyd-Cyc-Phe-CN IbN3-1 R ¹ -Pyr-Cyc-Phe-CN IbN3- 2 R ¹ -Phe-Pyd-Phe-CN IV5 R ¹ -Phe-Pyr-Phe-CN IV6 R ¹ -Cyc-Pyd-Phe-CN IV8 R ¹ -Cyc-Pyr-Phe-CN IV7 R ¹ -Pyd- Phe-CH ₂ CH ₂ -Phe-CN IbN3-3 R ¹ -Pyr-Phe-CH ₂ CH ₂ -Phe-CN IbN3-4 R ¹ -Pyd-Cyc-CH ₂ CH ₂ -Phe-CN IbN3-5 R ¹ -Pyr-Cyc-CH ₂ CH ₂ -Phe-CN IbN3-6 R ¹ -Phe-Pyd-CH ₂ CH ₂ -Phe-CN IbN3-7 R ¹ -Phe-Pyr-CH ₂ CH ₂ -Phe-CN IbN3-8 R ¹ -Cyc-Pyd-CH ₂ CH ₂ -Phe-CN IbN3-9 R ¹ -Cyc-Pyr-CH ₂ CH ₂ -Phe-CN IbN3-10 R ¹ -Pyd-CH ₂ CH ₂ -Phe -Phe-CN IbN3-11 R ¹ -Pyr-CH ₂ CH ₂ -Phe-Phe-CN IbN3-12 R ¹ -Pyd-CH ₂ CH ₂ -Cyc-Phe-CN IbN3-13 R ¹ -Pyr-CH ₂ CH ₂ -Cyc-Phe-CN IbN3-14 R ¹ -Phe-CH ₂ CH ₂ -Pyd-Phe-CN IbN3-15 R ¹ -Phe-CH ₂ CH ₂ -Pyr-Phe-CN IbN3-16 R ^1- Cyc-CH ₂ CH ₂ -Pyd-Phe-CN IbN3-17 R ¹ -Cyc-CH ₂ CH ₂ -Pyr-Phe-CN IbN3-18

Formulas IV3 to IV8 and IbN3-1 to Ib
In the compound of N3-18, R ¹ is methyl, ethyl,
Propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, heptoxy, octoxy, nonyloxy, decyloxy, methoxymethyl, ethoxymethyl, propoxymethyl, butoxymethyl, methoxyethyl , Ethoxyethyl or propoxyethyl.

The compound of the formula IbN is described in DE 3,600,05
2, DE 3,315,295, SU1,063,10
0, SU1, 063, 101, SU1, 069, 41
3, SU1,171,456, GB2,118,93
4, EP 0,097,033 and DE 3,411,5
Preferably, it is produced by the method described in 71.

Formulas IbN and IV, especially formulas IbN2-1 to IbN2-1
IbN2-2, IbN3-1 to IbN3-18 and IV
Liquid crystal mixtures containing one or more compounds selected from the compounds of 1 to IV8 have advantageous values for the optical anisotropy Δn,
It is characterized by high stability, low miscibility with the polymers used for the matrix, a wide mesogenic range, a relatively high clearing point and advantageous values for the dielectric anisotropy and advantageous temperature dependence of the electro-optical parameters. These mixtures are preferred.

The liquid crystal mixture of the present invention comprises 1 to 40%, especially 5%
３０30% of formulas IbN and IV, especially formulas IbN2-1 to I
bN2-2, IbN3-1 to IbN3-18 and IV1
It preferably contains the compounds of the formulas IV8 to IV8. in this case,
The liquid-crystal mixtures comprise 1 to 5, in particular 1 to 3, formula IbN and
IV, especially formulas IbN2-1 to IbN2-2, IbN3-1
ＩIbN3-18 and IV1-IV8.

Preferred compounds of the formulas IV3 to IV4 have a high or relatively high value for the dielectric anisotropy Δε. In this case, the structural element

[0129]

Embedded image IV6, IV7, IbN3-8, IbN3-
Compounds 16 and IbN3-18 are characterized by high values for Δε.

Particularly preferred compounds are those of formulas IV3, IV4, which are characterized by relatively high dielectric anisotropy and high optical anisotropy.
IV5, IV6, IbN3-3, IbN3-4, IbN3-
7, IbN3-8, IbN3-11, IbN3-12,
It is a compound of IbN3-15 and IbN3-16.
Liquid crystal mixtures containing these preferred compounds are particularly preferred.

Formulas IV3, IV4, IV5, IV6 and / or
Liquid crystal mixtures containing compounds of IV7 are sometimes not very suitable for network systems. On the other hand, liquid crystal mixtures of this kind are generally particularly suitable for application in matrix systems.

Formulas IbN, especially IbN2-1 to IbN2-
2, one or more compounds selected from IbN3-1 to IbN3-18 and IV1 to IV8, and further compounds II1 to II
Particularly preferred is a liquid crystal mixture comprising 28 and one or more compounds selected from the group of III1 to III3. Formulas IbN and I in the liquid crystal mixtures used according to the invention
V, especially the formulas IbN2-1 to IbN2-2, IbN3-1
The mass of the component mixture consisting of .about.IbN3-18 and at least one compound of IV1-IV8 and also of at least one compound of formulas II1-II28 and III1-III3 is 1
It is preferably from 5% to 100%, particularly preferably from 25% to 100%.

The following component mixture T (IbN) containing at least one compound from each of the indicated substance groups:
Is particularly suitable for application to matrix systems, but is less suitable for networked systems. R has the meaning described above.

[0134]

[Table 6]

Furthermore, at least one of each of the compounds of IbN and IV shown in each case
The following component mixtures containing certain compounds are less preferred for network systems.

[0136]

[Table 7]

Component mixture T (IbN) 9 to T (IbN)
12 is preferably applied to a matrix system.

The following component mixtures T each containing at least one compound from the abovementioned substance groups:
Liquid crystal mixtures containing one or more of (IbN) 13-18 are sometimes not very suitable for application to network systems.
In contrast, these liquid-crystal mixtures can generally be used favorably for application in matrix systems.

[0139]

[Table 8]

On the other hand, liquid crystal mixtures of this kind can often be modified by adding further compounds so that they are suitable for application to a network system.

Therefore, the above component mixture T (IbN)
In addition to 1 to 18, liquid-crystal mixtures containing, for example, one or more compounds selected from the group of the compounds of the formulas Ia, IbF, Ic, Id and Ie, particularly preferred sub-formulas, are generally applicable to network systems. Are suitable.

In addition to the above-mentioned component mixtures, liquid-crystal mixtures containing one or more compounds of the formula If, in particular the preferred sub-formulas, are also particularly suitable for application to the network system. The mass of the compound of formula If in these liquid-crystal mixtures is preferably at least 5%, in particular at least 7.5%, more particularly at least 10%.

The liquid-crystal mixtures used according to the invention, which contain one or more of the component mixtures T (IbN) 1 to 18, are generally particularly preferably applied to matrix systems.

At least one compound selected from the group consisting of compounds IV1, IV2, IV3, IV4, IV5 and IV6, and further compounds II5, II6, II7, II9, II11, II14,
Liquid crystal mixtures containing at least one compound selected from the group of II16, II22 and II23 are generally even less preferred for application to network systems, but such mixtures are not preferred for application to matrix systems. Particularly suitable. In contrast, the liquid crystals used according to the invention containing such component mixtures and furthermore one or more compounds selected from the group of the compounds of the formulas Ia, Ic, Id, Ie and IbF, particularly preferred lower formulas It is generally preferred that the mixture be applied to a network system. This also applies to liquid-crystal mixtures containing one or more compounds of the formula If, in particular the preferred subformulae. Formula If in a liquid crystal mixture
Is preferably at least 5%, more preferably at least 10%, even more preferably at least 12.5%.

Formulas IbN2-1, IbN2-2 and Ib
Liquid crystal mixtures containing at least one compound from N3-3 to IbN3-18 are particularly preferred for network systems and also for matrix systems.

Furthermore, the compounds of the formula IbN, especially IbN2-1, IbN
bN2-2 and IbN3-1 to IbN3-18 and
The following compounds other than one or more compounds of IV1 to IV8
II2, II4, II3, II8, II10, II15, II17, II
18, II19, II25, II26, II27, II28, III
1, III2, III3, II12, II13, II20, II21,
Liquid-crystal mixtures containing at least one compound selected from II24, IV7 and IV8 are particularly well suited for use in an electro-optical system according to the preamble of claim 1.

Preference is given to liquid-crystal mixtures based on the following component mixtures T (IbF) 19 to 23, each containing at least one compound from the compounds of the formulas mentioned in each case. The following table further shows the preferred masses of these compounds in the component mixture. Ingredient mixture is 2-3
It contains 8, preferably 2 to 35, especially 2 to 25 compounds. The sum of the masses of these compounds in the component mixture is 100%. The mass of the component mixture in the liquid crystals according to the invention is between 10% and 100%, in particular between 15% and 100%, more particularly between 25% and 100%.

[0148]

[Table 9] Those liquid crystal mixtures have the formula Ic

[0149]

Embedded image [Where Q ³ is

[0150]

Embedded image And one of ring A ⁷ or ring A ⁸ is

[0151]

Embedded image (Where T ¹ is —CH ₂ — or —O—) and the other, if present, is trans-1,4-
Cyclohexylene or 1,4-phenylene, 2-fluoro-1,4-phenylene or 3-fluoro-1,4
- phenylene, Z ⁷ and Z ⁸ are each independently a single bond, -COO -, - OCO- or -CH ₂ CH ₂ -
And r and q are, independently of one another, 0 or 1, X ³ is F or Cl, and

[0152]

Embedded image Is 2-fluoro- or 2-chloro-1,4-phenylene or 3-fluoro- or 3-chloro-1,4-phenylene, and R ¹ has the meaning given in claim 1]. The electro-optical liquid-crystal systems according to the invention which comprise a class of compounds are more particularly suitable.

Compounds of the formula Ic have the meaning that Z ⁷ and X ³ have the meanings given above and Phe. (X) is Phe, Phe.
F or Phe. The following formulas IcT2 and I which are Cl
Includes bicyclic tetrahydropyran derivatives and dioxane derivatives of cD2.

R ¹ -Thp-Z ⁷ -Phe. (X) -CN IcT2R ¹ -Dio
-Z ⁷ -Phe. (X) -CN IcD2 Formulas IcT2 and IcD2
In the compounds of formula (I), R ¹ is preferably alkyl or alkoxy having ¹ to 10, especially 1 to 8, C atoms. n
-Alkoxyalkyl compounds, especially n-alkoxymethyl and n-alkoxyethyl compounds, are more preferred. Further, R is also preferably alkenyl having 1 to 7 C atoms. R is methyl, ethyl, propyl,
Compounds which are butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, heptoxy or octoxy are particularly highly preferred compounds of the formulas IcT2 and IcD2.

In the compounds of the formulas IcT2 and IcD2, Z represents --CH ₂ CH _2- , --COO--, --OCO-- or a single bond, in particular --CH ₂ CH _2- , --COO-- or a single bond, more particularly —COO— or a single bond. The phenyl ring is monosubstituted by X ³ F or Cl (r =
1) can be substituted or unsubstituted. Unsubstituted compounds and compounds having an F atom at two or three sites or a Cl atom at three sites are preferred.

Formulas IcT2-1 to IcT2-5 and Ic
The following small group of compounds of D2-1 to IcD2-6 are particularly preferred.

R ¹ -Thp-Phe-CN IcT2-1 R ¹ -Thp-Phe.3F-CN IcT2-2 R ¹ -Thp-Phe.3Cl-CN IcT2-3 R ¹ -Thp-COO-Phe. F) -CN IcT2-4 R ¹ -Thp-CH ₂ CH ₂ -Phe. (F) -CN IcT2-5 R ¹ -Dio-Phe-CN IcD2-1 R ¹ -Dio-Phe.3F-CN IcD2- 2 R ¹ -Dio-Phe.3Cl-CN IcD2-3 R ¹ -Dio-COO-Phe.3F-CN IcD2-4 R ¹ -Dio-COO-Phe.3Cl-CN IcD2-5 R ¹ -Dio-CH ₂ CH ₂ -Phe. (F) -CN IcD2-6

Formulas IcT2-1 to IcT2-5 and Ic
Liquid crystal mixtures containing one or more compounds selected from the group of preferred compounds D2-1 to IcD2-6 are particularly preferred. Compounds IcT2-1, IcT2-2, IcT2-
4, IcT2-5, IcD2-1, IcD2-2, Ic
Mixtures containing compounds selected from the group of D2-4 and IcD2-6 are particularly highly preferred liquid crystal mixtures.

The compound of formula Ic is further represented by the following formula IcT3-1
To IcT3-8 and IcD3-1 to IcD3-8
Including cyclic tetrahydropyran derivatives and dioxane derivatives.

R ¹ -Phe. (F) -Thp-Z ⁷ -Phe. (X) -CN IcT3-1 R ¹ -Cyc-Thp-Z ⁷ -Phe. (X) -CN IcT3-2 R ^1- Thp-Phe. (F) -Z ⁷ -Phe. (X) -CN IcT3-3 R ¹ -Thp-Cyc-Z ⁷ -Phe. (X) -CN IcT3-4 R ¹ -Phe. (F)- Z ⁸ -Thp-Phe. (X) -CN IcT3-5 R ¹ -Cyc-Z ⁸ -Thp-Phe. (X) -CN IcT3-6 R ¹ -Thp-Z ⁸ -Phe. (F) -Phe . (X) -CN IcT3-7 R ¹ -Thp-Z ⁸ -Cyc-Phe. (X) -CN IcT3-8 R ¹ -Phe. (F) -Dio-Z ⁷ -Phe. (X) -CN IcD3-1 R ¹ -Cyc-Dio-Z ⁷ -Phe. (X) -CN IcD3-2 R ¹ -Dio-Phe. (F) -Z ⁷ -Phe. (X) -CN IcD3-3 R ^1- Dio-Cyc-Z ⁷ -Phe. (X) -CN IcD3-4 R ¹ -Phe. (F) -Z ⁸ -Dio-Phe. (X) -CN IcD3-5 R ¹ -Cyc-Z ⁸ -Dio -Phe. (X) -CN IcD3-6 R ¹ -Dio-Z ⁸ -Phe. (F) -Phe. (X) -CN IcD3-7 R ¹ -Dio-Z ⁸ -Cyc-Phe. (X) -CN IcD3-8

Formulas IcT3-1 to IcT3-8 and Ic
In preferred compounds of D3-1 to IcD3-8, R
¹ is methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, heptoxy, octoxy, nonyloxy, decyloxy, methoxymethyl, ethoxymethyl, propoxymethyl Butoxymethyl, methoxymethyl, ethoxymethyl, propoxymethyl, butoxymethyl, methoxymethoxyethyl, ethoxyethyl, propoxyethyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl or Preferably it is 5-hexenyl. Formula IcT3
-1 to IcT3-8 and IcD3-1 to IcD3-8
Wherein Z ⁷ and Z ⁸ are -COO-, -OCO
-, - CH ₂ CH ₂ - or a single bond, preferably -COO
—, —CH ₂ CH ₂ — or a single bond, more particularly a single bond.

Phe. Formulas IcT3-1 to IcT, wherein (F) is a 2- or 3-fluoro-1,4-phenylene group
Compounds 3-8 and IcD3-1 to IcD3-8 generally have relatively lower viscosities η as compared to non-laterally substituted compounds.

The following subgroup of tricyclic compounds is particularly highly preferred.

R ¹ -Phe-Thp-Phe-CN IcT3-1a R ¹ -Phe-Thp-Phe.3F-CN IcT3-1b R ¹ -Phe-Dio-Phe-CN IcD3-1a R ¹ -Phe-Dio -Phe.3F-CN IcD3-1b R ¹ -Cyc-Thp-Phe-CN IcT3-2a R ¹ -Cyc-Dio-Phe-CN IcD3-2a R ¹ -Thp-Phe-Phe-CN IcT3-3a R ¹ -Dio-Phe-Phe-CN IcD3-3a R ¹ -Dio-Phe-Phe.3F-CN IcD3-3b

When Z ⁷ and Z ⁸ represent —COO— or —CH ₂ C
H ₂ - a is Formula IcT3-1, IcD3-1, IcT3
-3, IcD3-3, IcT3-5, IcD3-5, I
The tetrahydropyrans and dioxanes of cT3-6 and IcD3-6 are more particularly highly preferred.

Formulas IcT2, IcD2, IcT3 and I
The compounds of cD3 have advantageous values for the flow viscosity η and the optical anisotropy Δn and especially high values for the dielectric anisotropy Δε. Structural element

[0167]

Embedded image Formulas IcT2, IcD2, IcT3 and IcD3 comprising
Have particularly very high values for Δε.

Compounds of formula IcT or IcD are of the type DE3,
447,359, DE3,306,960, GB89
It is preferably prepared by the method described in US Pat. No. 2,583.7 and DE 3,146,249.

Formulas IcT2, IcD2, IcT3 and I
cD3, more particularly the preferred formulas IcT2-1 to Ic
T2-5, IcD2-1 to IcC2-6, IcT3-1
a-1b, IcD3-1a-1b, IcT3-2a, I
cD3-2a, IcT3-3a and IcD3-3a-
Liquid crystal mixtures containing at least one compound of 3b have advantageous values for the birefringence Δn and the flow viscosity η, high stability, low miscibility with the polymers used for the matrix, wide mesogenic range, relatively high clearing points,
And especially advantageous values for the dielectric anisotropy and the temperature dependence of the electro-optical parameters.

The liquid-crystal mixtures used in the electro-optical liquid-crystal systems according to the invention preferably contain from 1 to 40%, in particular from 5 to 30%, of the compounds of the formulas IcT and IcD, particularly the preferred subformulae. In this case, the liquid crystal mixture has the formulas IcT and Ic
It is preferred to contain D, in particular from 1 to 5, especially from 1 to 3, compounds of the particularly preferred sub-formula.

Formulas IcT2, IcD2, IcT3 and I
cD3, particularly preferred formulas IcT2-1 to IcT2-5,
IcD2-1 to IcC2-6, IcT3-1a to 1b,
IcD3-1a-1b, IcT3-2a, IcD3-2
a, one or more compounds selected from the group of compounds IcT3-3a and IcD3-3a-3b, and further compounds II
A mixture containing at least one compound selected from the group consisting of 1 to II28, III1 to III3 and IV1 to IV8 is a particularly preferred liquid crystal mixture. Formulas IcT2, IcD2, IcT3 and I in the liquid crystal mixture used according to the invention
cD3, in particular at least one compound of the preferred sub-formula indicated, and additionally formulas II1-II28, III1-III3 and
The weight of the component mixture consisting of at least one compound of IV1 to IV8 is from 15% to 100%, in particular from 25% to 100%
It is preferred that

The following component mixtures containing at least one compound from Group A below and at least one compound from Group B below are particularly preferred.

[0173]

[Table 10]

Preference is given to liquid-crystal mixtures based on the following component mixtures T (Ic) 1 to 5, each containing at least one compound from the compounds of the formulas mentioned in each case. The following table further shows the preferred masses of these compounds in the component mixture. The component mixture contains 2 to 38, preferably 2 to 35, especially 2 to 25 compounds. The sum of the masses of these compounds in the component mixture is 1
00%. The mass of the component mixture in the liquid crystal of the present invention is 1
It is between 0% and 100%, especially between 15% and 100%, more particularly between 25% and 100%.

[0175]

[Table 11] Those liquid crystal mixtures have the formula Id

[0176]

Embedded image (In the formula, ring A ⁹ is 1,4-phenylene or trans-
1,4-cyclohexylene, and ring A ¹⁰ is 1,4-phenylene, 2-fluoro-1,4-phenylene, 3-fluoro-1,4-phenylene or trans-1,4-
Cyclohexylene, Z ⁹ is a single bond, -COO-,
-OCO- or -CH ₂ CH ₂ - and is, Z ¹⁰ represents a single bond, -COO- or -CH ₂ CH ₂ - and is, s is 0 or 1, and R ¹ is meanings given above) More preferred are electro-optical liquid crystal systems comprising one or more compounds of the formula:

The liquid crystal is represented by the formulas IdE2-1 and IdE3-1
1 selected from the following subgroups of compounds:
Systems containing more than one compound are particularly preferred systems.

R ¹ -Cyc-CH ₂ CH ₂ -Phe-CN IdE2-1 R ¹ -Cyc-CH ₂ CH ₂ -Phe-Phe-CN IdE3-1 R ¹ -Phe-CH ₂ CH ₂ -Cyc-Phe -CN IdE3-2 R ¹ -Cyc-CH ₂ CH ₂ -Cyc-Phe-CN IdE3-3 R ¹ -Cyc-Phe-CH ₂ CH ₂ -Phe-CN IdE3-4 R ¹ -Phe-Cyc-CH ₂ CH ₂ -Phe-CN IdE3-5 R ¹ -Cyc-Cyc-CH ₂ CH ₂ -Phe-CN IdE3-6 R ¹ -Phe-Phe-CH ₂ CH ₂ -Phe-CN IdE3-7 R ¹ -Phe- CH ₂ CH ₂ -Phe-Phe-CN IdE3-8, wherein R ¹ has the meaning given above.

In the bicyclic compound of the formula IdE2-1,
R ¹ is preferably n-alkyl or n-alkoxy having ¹ to 10 C atoms, in particular 1 to 8 C atoms. More preferred are n-alkoxyalkyl compounds, especially n-alkoxymethyl and n-alkoxyethyl compounds.

In the tricyclic compounds of the formulas IdE3-1 to IdE3-8, R ¹ is an n having ¹ to 10 C atoms.
-Alkyl or n-alkoxy, preferably
Furthermore, n-alkoxy having 1 to 6 C atoms
It is also an alkoxymethyl or n-alkoxyethyl.

R ¹ is methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, heptoxy, octoxy, methoxymethyl, ethoxymethyl, propoxymethyl , Butoxymethyl, methoxymethyl, ethoxymethyl or propoxymethyl.

The compounds of the formulas IdE2 and IdE3 are
2,636,684, DE2,922,236, EP
0,102,047, EP0,129,177, DE
3,040,362, DE 3,317,597 and U
It is preferable to produce by the method described in S4,035,056.

Formulas IdE2-1 and IdE3-1 to Id
Liquid-crystal mixtures containing at least one compound selected from the compounds of E3-8 have advantageous values for the dielectric anisotropy Δε, high stability, low miscibility with the polymers used for the matrix, and a particularly wide mesogenic range , Characterized by a relatively high clearing point and advantageous values for birefringence.

The liquid-crystal mixtures used in the electro-optical liquid-crystal systems according to the invention preferably contain from 1 to 40%, in particular from 5 to 30%, of the compounds of the formula Id, particularly preferred lower formulas. In this case, the liquid crystal mixture is of the formula Id, particularly the preferred subformulas 1 to
It preferably contains five, especially one to three, compounds.

Formulas IdE2-1 and IdE3-1 to Id
At least one compound selected from the group of compounds of E3-8 and further compounds II1-II28, III1-III3 and IV1-
Mixtures containing one or more compounds selected from the group of IV8 are particularly preferred liquid crystal mixtures. Formulas IdE2-1 and IdE3-1 to IdE in liquid crystal mixtures according to the invention
3-8 at least one compound of the formula II1-2
8, at least one compound of III1 to III3 and IV1 to IV8 has a mass of 15% to 100%
%, Especially 25% to 100%.

The following component mixtures, T (IdE), containing at least one compound each selected from the group of compounds indicated in each case, are particularly suitable for application to matrix systems, Especially very suitable to apply to.

[0187]

[Table 12]

The following component mixtures, which contain one or more compounds selected in each case from the compounds indicated, are very particularly suitable for application to matrix systems.

[0189]

[Table 13]

For application in both matrix systems and especially network systems, at least one compound of the formula IdE2-1 and compounds II1, II3-II5, II7-II28
And a liquid crystal mixture containing at least one compound selected from the group of IV1 to IV6. The properties of these mixtures can generally be further improved by the addition of one or more compounds selected from the compounds of the formulas Ia, IbF, Ic, Id and If, especially preferred subformulae.

Furthermore, the following component mixtures T (IdE) 17 to 17 each containing at least one compound of the formulas indicated in each case within the indicated mass percent range:
T (IdE) 19 is very particularly preferred. In this case, the sum of the masses of the component mixtures is 100% for each component mixture.
It is. On the other hand, the mass of the component mixture in the liquid crystal mixture used in the system of the present invention is 10% to 100%, particularly 10% to 9%.
0%, more particularly 15% to 85%.

[0192]

[Table 14] Those liquid crystal mixtures have the formulas Ie4-1 to Ie4-4

[0193]

Embedded image (Wherein ring A ¹¹ is in each case independently of one another
1,4-phenylene, 2-fluoro-1,4-phenylene, 3-fluoro-1,4-phenylene or trans-1,4-cyclohexylene, the rings A ¹² being in each case independently of one another ,

[0194]

Embedded image And t is 0 or 1, and

[0195]

Embedded image Is 2-fluoro-1,4-phenylene or 3-fluoro-1,4-phenylene, and R ¹ is
Further preferred is an electro-optical liquid crystal system comprising one or more tri- or tetracyclic compounds selected from the group of the carbonitrile compounds (meaning indicated in the above).

Formulas Ie4-1a to Ie4-1 shown below
g, Ie4-2a to Ie4-2k, Ie4-3a to Ie
Compounds of 4-3f and Ie4-4a to Ie4-4l are particularly preferred.

R ¹ -Phe-Phe-Phe-CH ₂ CH ₂ -Phe-CN Ie4-1a R ¹ -Phe-Phe-Phe.2F-CH ₂ CH ₂ -Phe-CN Ie4-1b R ¹ -Phe- Phe-Phe.3F-CH ₂ CH ₂ -Phe-CN Ie4-1c R ¹ -Phe-Phe-Phe-CH ₂ CH ₂ -Phe.F-CN Ie4-1d R ¹ -Phe-Phe-Cyc-CH ₂ CH ₂ -Phe-CN Ie4-1e R ¹ -Cyc-Phe-Phe. (F) -CH ₂ CH ₂ -Phe. (F) -CN Ie4-1f R ¹ -Cyc-Cyc-Phe. (F)- CH ₂ CH ₂ -Phe-CN Ie4-1g R ¹ -Phe-CH ₂ CH ₂ -Phe-Phe. (F) -Phe. (F) -CN Ie4-2a R ¹ -Phe-CH ₂ CH ₂ -Cyc -Phe-Phe-CN Ie4-2b R ¹ -Cyc-CH ₂ CH ₂ -Phe-Phe.2F-Phe-CN Ie4-2c R ¹ -Cyc-CH ₂ CH ₂ -Phe-Phe.3F-Phe-CN Ie4-2d R ¹ -Cyc-CH ₂ CH ₂ -Phe-Phe-Phe. (F) -CN Ie4-2e R ¹ -Cyc-CH ₂ CH ₂ -Phe-Cyc-Phe-CN Ie4-2f R ^1- Cyc-CH ₂ CH ₂ -Cyc-Phe-Phe-CN Ie4-2g R ¹ -Cyc-CH ₂ CH ₂ -Cyc-Phe.2F-Phe-CN Ie4-2h R ¹ -Cyc-CH ₂ CH ₂ -Cyc -Phe.3F-Phe-CN Ie4-2i R ¹ -Cyc-CH ₂ CH ₂ -Cyc-Phe-Phe. (F) -CN Ie4-2k R ¹ -Phe-CH ₂ CH ₂ -Phe-Phe. F) -CH ₂ CH ₂ -Phe-CN Ie4-3a R ¹ -Phe-CH ₂ CH ₂ -Cyc-Phe. (F) -CH ₂ CH ₂ -Phe-CN Ie4-3b R ¹ -Cyc-CH ₂ CH ₂ -Phe-Phe-CH ₂ CH ₂ -Phe-CN Ie4-3c R ¹ -Cyc-CH ₂ CH ₂ -Phe-Phe.2F-CH ₂ CH ₂ -Phe-CN Ie4 -3d R ¹ -Cyc-CH ₂ CH ₂ -Phe-Phe.3F-CH ₂ CH ₂ -Phe-CN Ie4-3e R ¹ -Cyc-CH ₂ CH ₂ -Cyc-Phe. (F) -CH ₂ CH ₂ -Phe-CN Ie4-3f R ¹ -Phe-Phe-CH ₂ CH ₂ -Phe-Phe-CN Ie4-4a R ¹ -Phe-Phe-CH ₂ CH ₂ -Ph e.2F-Phe-CN Ie4- 4b R ¹ -Phe-Phe-CH ₂ CH ₂ -Phe.3F-Phe-CN Ie4-4c R ¹ -Phe-Phe-CH ₂ CH ₂ -Cyc-Phe-CN Ie4-4d R ¹ -Cyc-Phe- CH ₂ CH ₂ -Phe. (F) -Phe-CN Ie4-4e R ¹ -Cyc-Phe-CH ₂ CH ₂ -Cyc-Phe-CN Ie4-4f R ¹ -Phe-Cyc-CH ₂ CH ₂ -Phe -Phe-CN Ie4-4g R ¹ -Phe-Cyc-CH ₂ CH ₂ -Cyc-Phe-CN Ie4-4h R ¹ -Cyc-Phe-CH ₂ CH ₂ -Phe-Cyc-CN Ie4-4i R ^1- Cyc-Phe-CH ₂ CH ₂ -Phe.2F-Cyc-CN Ie4-4k R ¹ -Cyc-Phe-CH ₂ CH ₂ -Phe.3F-Cyc-CN Ie4-4l

Formulas Ie4-1a to Ie4-1g, Ie4-
In the compounds of 2a to Ie4-2k, Ie4-3a to Ie4-3f and Ie4-4a to Ie4-4l, R ¹ is 1 to 1.
Preference is given to alkyl or alkoxy having 0, especially 1 to 8, C atoms. More preferred are n-alkoxyalkyl compounds, especially n-alkoxymethyl and n-alkoxyethyl compounds.

The compounds of the formulas Ie4-1 to Ie4-4 are
It is preferably produced by the methods described in DE 3,401,320 and DE 2,617,593.

Formulas Ie4-1 to Ie4-4, especially compounds of the formula Ie4
-1a to Ie4-1g, Ie4-2a to Ie4-2k,
Ie4-3a to Ie4-3f and Ie4-4a to Ie
Liquid crystal mixtures containing one or more compounds selected from the group of 4-4 l are preferred. Formula Ie4-1, Ie4
-2 and Ie4-4, especially formulas Ie4-1a to Ie4-
1g, Ie4-2a to Ie4-2k and Ie4-4a
Liquid crystal mixtures containing one or more compounds selected from the group consisting of -Ie4-4l are particularly preferred.

The compounds of the formulas Ie4-1 to Ie4-4 have high clearing points and relatively high values for the flow viscosity η.

In order to lower the flow viscosity, the formula Ie4-
The 1,4-phenylene group of the compound of 1 to Ie4-4 is represented by X =
Lateral mono-substitution with F or Cl, especially F, is also possible. The substituted compounds have the following structural features S1-S
3

[0203]

Embedded image It is particularly preferred to have one of the following:

The liquid crystal of the present invention accounts for 2 to 40%, especially 5 to 30%.
% Of Formulas Ie4-1a to Ie4-1g, Ie4-2a to Ie
e4-2k, Ie4-3a to Ie4-3f and Ie4
-4a to Ie4-41 preferably contain a compound selected from the group of tetracyclic carbonitriles. In this case, the liquid crystal preferably contains 1 to 5, especially 1 to 3, compounds of the formula Ie4 and the preferred sub-formulae.

The choice of the compounds of the formulas Ie4-1 to Ie4-4, particularly preferred lower formulas, is made in view of the particular embodiment of the electro-optical system of the invention which is desired in each case. For example, if a high viscosity and high clearing point liquid crystal medium having high optical anisotropy is required, the medium may be, for example, particularly Ie4
-1a, Ie4-2a, Ie4-3a and / or I
e4-4a including one or more laterally unsubstituted compounds. On the other hand, a high clearing point medium having a relatively low viscosity and a relatively low optical anisotropy is represented by the formula Ie4-1
g, Ie4-2h-2k, Ie4-3f and / or Ie4-4i-4l preferably comprise one or more laterally mono-substituted compounds. Formulas Ie4-1 to Ie4-1
Ie4-3, especially formulas Ie4-1a to Ie4-1g, Ie
4-2a to Ie4-2k, Ie4-3a to Ie4-3f
And Ie4-4a to Ie4-4l, more particularly formulas Ie4-1a to Ie4-1g, Ie4-2a to Ie4-
2k and one or more compounds selected from the group of compounds Ie4-4a to Ie4-4l and further compounds II1 to II2
8, a mixture containing at least one compound selected from the group consisting of III to III3 and IV1 to IV8 is a particularly preferred liquid crystal mixture. In the liquid-crystal mixtures used according to the invention, at least one compound of the formulas 1e4-1 to Ie4-4, particularly preferred subformulae, and furthermore formulas II1 to II28, III
The mass of the component mixture comprising at least one compound of the formulas 1 to III3 and IV1 to IV8 is preferably from 15% to 100%, particularly preferably from 25% to 100%.

In addition to the compounds of the formulas Ie4-1 to Ie4-4, in particular at least one compound selected from the group of compounds of the sub-formulae of these compounds, the compounds of the formulas II1 to II6, II7, II
9, II11, II14, II16, II23, II22 and IV
The following component mixtures T (Ie4) containing one or more compounds selected from the compounds 1 to IV8 are very particularly preferred.

Preference is given to liquid-crystal mixtures based on the following component mixtures T (Ie4) 1-3, each containing at least one compound from the compounds of the formulas mentioned in each case. The following table further shows the preferred masses of these compounds in the component mixture. The component mixture is 2 to 38 types,
It preferably contains 2 to 35, especially 2 to 25 compounds. The sum of the masses of these compounds in the component mixture is 100%. The mass of the component mixture in the liquid crystals according to the invention is between 10% and 100%, in particular between 15% and 100%, more particularly between 25% and 100%.

[0208]

[Table 15] Those liquid crystal mixtures have the formula If

[0209]

Embedded image (Wherein at least one of ring A ¹³ and, if present, ring A ¹⁴ is 1,4-phenylene, 2-fluoro-1,4
-Phenylene, 3-fluoro-1,4-phenylene, trans-1,4-cyclohexylene, pyridine-2,5
-Diyl, pyrimidine-2,5-diyl or 1,3-
Dioxane-2,5-diyl and the other, if present, trans-1,4-cyclohexylene,
1,4-phenylene, 2-fluoro-1,4-phenylene or 3-fluoro-1,4-phenylene, and Z
¹¹ and Z ¹² are in each case independently of one another a single bond, -C≡C-, -CH ₂ CH _2- , -COO-, -OC
O- or a combination of two or more of these bridge members, v is 0, 1 or 2, a is 0 or 1,

[0210]

Embedded image Is 2-fluoro-1,4-phenylene or 3-fluoro-1,4-phenylene,

[0211]

Embedded image Is 3,5-difluoro-1,4-phenylene, and T ² is —Cl, —F, —CF ₃ , —OCF ₃ , —OC
Further preferred is an electro-optical liquid crystal system comprising one or more compounds of HF ₂ or NCS and R ¹ has the meaning given in claim 1).

Hereinafter, Phe. (F, 2) is a 1,4-phenylene group which is not laterally substituted, a 1,4-phenylene group which is laterally monosubstituted at 2 or 3 positions, or a 1,4-phenylene group which is laterally disubstituted at 3 and 5 positions. 4-phenylene group.

The following compounds wherein T ² is --NCS are of the formula I
Preferred compounds of f.

[0214]

Embedded image Compounds of formula IfI are preferably of the following formulas IfI2-1 to IfI
2-4 bicyclic compounds.

R ¹ -Phe-Z ¹¹ -Phe-NCS IfI2-1 R ¹ -Cyc-Z ¹¹ -Phe-NCS IfI2-2 R ¹ -Pyr-Z ¹¹ -Phe-NCS IfI2-3 R ¹ -Pyd- Z ¹¹ -Phe-NCS IfI2-4 R ¹ is preferably a linear group, more preferably 1 to 10, especially 1 to 8
Preference is given to alkyl or alkoxy having 3 C atoms. n-alkoxyalkyl compounds, in particular n-
Alkoxymethyl and n-alkoxyethyl compounds are more preferred.

In the compounds of the formulas IfI2-1 to IfI2-4, Z ¹¹ is preferably a single bond, —CH ₂ CH ₂ —, COO or OCO. Z is a single bond or COO,
In particular, liquid-crystal mixtures containing one or more compounds of the formula IfI2-3 or IfI2-4, which are single bonds, have a dielectric anisotropy Δ
It has a particularly advantageous value for ε.

Compounds of the formulas IfI2-1 and IfI2-2 are particularly preferred. Formulas IfI2-1a-1b and If
The following small group of bicyclic compounds of I2-2a-2b are particularly highly preferred.

R ¹ -Phe-Phe. (F) -NCS IfI2-1a R ¹ -Phe-Phe. (F) -NCS IfI2-1b R ¹ -Cyc-Phe. (F) -NCS IfI2-2a R ¹ -Cyc-CH ₂ CH ₂ -Phe. (F) -NCS IfI2-2b

In addition to one or more laterally non-fluorinated compounds of the formula IfI2-2a, the compounds of the formulas II5, IV1 and
Liquid crystal mixtures containing at least one compound selected from the group of compounds of IV2 are particularly suitable for matrix systems, but are less suitable for network systems.

Compounds of formula IfI are of the following formulas IfI3-1 to IfI3-1
It further includes a tricyclic compound of fI3-20.

R ¹ -Phe-Phe-Z ¹² -Phe. (F) -NCS IfI3-1 R ¹ -Phe-Cyc-Z ¹² -Phe. (F) -NCS IfI3-2 R ¹ -Phe-Pyr- Z ¹² -Phe. (F) -NCS IfI3-3 R ¹ -Phe-Pyd-Z ¹² -Phe. (F) -NCS IfI3-4 R ¹ -Cyc-Phe-Z ¹² -Phe. (F) -NCS IfI3-5 R ¹ -Cyc-Cyc-Z ¹² -Phe. (F) -NCS IfI3-6 R ¹ -Cyc-Pyr-Z ¹² -Phe. (F) -NCS IfI3-7 R ¹ -Cyc-Pyd- Z ¹² -Phe. (F) -NCS IfI3-8 R ¹ -Pyr-Phe-Z ¹² -Phe. (F) -NCS IfI3-9 R ¹ -Pyd-Phe-Z ¹² -Phe. (F) -NCS IfI3-10 R ¹ -Phe-Z ¹¹ -Phe-Phe. (F) -NCS IfI3-11 R ¹ -Phe-Z ¹¹ -Cyc-Phe. (F) -NCS IfI3-12 R ¹ -Phe-Z ¹¹ -Pyr-Phe. (F) -NCS IfI3-13 R ¹ -Phe-Z ¹¹ -Pyd-Phe. (F) -NCS IfI3-14 R ¹ -Cyc-Z ¹¹ -Phe-Phe. (F) -NCS IfI3-15 R ¹ -Cyc-Z ¹¹ -Cyc-Phe. (F) -NCS IfI3-16 R ¹ -Cyc-Z ¹¹ -Pyr-Phe. (F) -NCS IfI3-17 R ¹ -Cyc-Z ¹¹ -Pyd-Phe. (F) -NCS IfI3-18 R ¹ -Pyr-Z ¹¹ -Phe-Phe. (F) -NCS IfI3-19 R ¹ -Pyd-Z ¹¹ -Phe-Phe. (F) -NCS IfI3-20

In the compounds of the formulas IfI3-1 to IfI3-20, R ¹ is preferably n-alkyl or n-alkoxy having ¹ to 10 C atoms,
N-alkoxymethyl having up to 8 C atoms or n
It is also an alkoxyethyl. R ¹ is methyl, ethyl,
Propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, heptoxy, octoxy, methoxymethyl, ethoxymethyl, propoxymethyl, butoxymethyl, methoxyethyl, ethoxyethyl or Formula IfI3 which is propoxyethyl
Compounds of -1 to IfI3-20 are particularly preferred compounds.

Formulas IfI3-1, IfI3-5, IfI3
Compounds of -11 and If13-15 are particularly preferred.
Z ¹¹ and Z ¹² are each independently a single bond or CO 2
O, in particular compounds of the formula IfI3 which are single bonds and of the formula If
The compounds of I3-13 have particularly advantageous values for Δε, especially when the terminal 1,4-phenylene group is fluorinated at three sites.

Formulas IfI3-1a, IfI3-1b, If
Very particular preference is given to the following subgroups of tricyclic compounds of I3-5a, IfI3-5b, IfI3-11a and IfI3-15a.

R ¹ -Phe-Phe-Phe. (F) -NCS IfI3-1a R ¹ -Phe-Phe-CH ₂ CH ₂ -Phe. (F) -NCS IfI3-1b R ¹ -Cyc-Phe-Phe . (F) -NCS If I3-5a R ¹ -Cyc-Phe-CH ₂ CH ₂ -Phe. (F) -NCS IfI3-5b R ¹ -Cyc-Cyc-Phe. (F) -NCS IfI3-6a R ¹ -Cyc-Cyc-CH ₂ CH ₂ -Phe. (F) -NCS IfI3-6b R ¹ -Phe-CH ₂ CH ₂ -Phe-Phe. (F) -NCS IfI3-11a R ¹ -Cyc-CH _{2 CH 2 -Phe-Phe. (F} ) -NCS IfI3-15a compound of formula IfI is EP0,169,327, JP61
189263, EP0, 126, 883, EP0, 2
15,800, DE327,115,10, EP0,2
42,716, DE3,545,345, EP0,22
7,004, EP 0,272,580 and DE 3,9
It is preferably produced by the method described in US Pat.

The choice of the compounds of formula IfI, particularly the preferred subformulae, is made in view of the particular embodiments of the electro-optical system of the present invention. For example, if a liquid crystal medium with a high or relatively high optical viscosity is required, the medium may be of the formula IfI2-1, IfI2-3, IfI3-, especially where Z is a single bond.
1, IfI3-3, IfI3-9, IfI3-11, I
fI3-13 and / or IfI3-19. Particularly preferred compounds are the terminal 1,
A compound in which a 4-phenyl group or another 1,4-phenylene group is laterally fluorine-substituted at two or three sites, particularly three sites. One skilled in the art will appreciate the pooled formula IfI
Other embodiments can be selected from the compounds of the present invention without inventive assistance.

Liquid crystalline mixtures containing one or more compounds of the formula IfI, particularly preferred subformulae, have advantageous values for the birefringence Δn and the dielectric anisotropy Δε, high stability, low miscibility with the polymers used in the matrix. And particularly advantageous values for the wide mesogenic range, relatively high clearing point, dielectric anisotropy and flow viscosity η.

These liquid crystal mixtures have a content of 1 to 40%, especially 5%.
It preferably comprises 〜30% of the compounds of the formula IfI, particularly the preferred subformulae. In this case, the liquid crystal mixture has the formula If
It is preferred that I contain 1 to 5, especially 1 to 3, compounds of the particularly preferred sub-formula.

Formulas IfI, especially IfI2-1 to IfI2
-4 and IfI3-1 to IfI3-20, more particularly the compounds IfI2-1a, IfI2-1b, IfI2-2.
a, IfI2-2b, IfI3-1a, IfI3-1
b, IfI3-5a, IfI3-5b, IfI3-11
a and 1 selected from the compound group of IfI3-15a
At least one compound and further compounds II1-II28, III1-I
Mixtures containing one or more compounds selected from the group of II3 and IV1 to IV8 are particularly preferred. Formulas IfI2 and IfI3 in the liquid crystal mixtures used according to the invention
A mass of a component mixture of at least one compound of the preferred subformula of these compounds, in particular with at least one compound of the formulas II1 to II28, III1 to III3 and IV1 to IV8, in particular from 15% to 100%, Especially 25% to 10
It is preferably 0%.

In addition to at least one laterally non-fluorinated compound selected from the group of compounds of the formulas IfI2-2a, IfI3-5a and IfI3-6a, the compounds of the formula II
5, at least one selected from the group consisting of IV1 and IV2
Liquid crystal mixtures containing certain compounds are generally particularly suitable for matrix systems, but are often less suitable for network systems. However, the properties of such component mixtures are characterized by at least one selected from the group of compounds of the formulas Ia, Ic, Id, Ie, IfF, IfCl and IfCl.
The addition of a species, preferably three or more compounds, is often clearly improved and also preferred for networks.

Compounds of Formulas IfI2-1b and IfI3-6b and Formulas
At least one compound selected from the group consisting of laterally fluorinated compounds of IfI2-1a and IfI3-6a, and further II1, II3, II2, II5, II9, II11, II14, II16, I
Liquid crystal mixtures containing compounds selected from the group of compounds I22, II23 and IV1 to IV8 are particularly suitable for matrix systems and very particularly suitable for network systems.

Furthermore, the following component mixtures, each containing at least one compound from the indicated group of compounds, are particularly suitable for both matrix systems and network systems.

[0233]

[Table 16]

[0234]

[Table 17] Compounds in which T ² is -UF

[0235]

Embedded image Wherein U is a single bond, —CF ₂ —, —OCF ₂ — or —OCHF—, and R ¹ has the meaning given in claim 1, is a further preferred compound of formula If.

The compounds of formula IfF are preferably represented by the following formulas IfF2-1 to IfF
2-4 bicyclic compounds.

[0237]

Embedded image In the compounds of the formulas IfF2-1 to IfF2-4, R ¹ is preferably a linear group, preferably an alkyl or alkoxy having 1 to 10, especially 1 to 8, C atoms. More preferred are n-alkoxyalkyl compounds, especially n-alkoxymethyl and n-alkoxyethyl compounds. Z ¹¹ is -
CH ₂ CH _2- , -C OO- or single bond, especially single bond or -CH ₂ C
It is preferably H ₂ —, more particularly a single bond. Ring A ¹³
Is preferably Cyc, Phe. (F), Pyr or Pyd.

The compounds of formula IfF are represented by the following small group of preferred compounds of formula I:
It further includes tricyclic compounds of fF3-1 to IfF3-8.

[0239]

Embedded image In the compounds of formulas IfF3-1 to IfF3-8, R ¹ is 1 to 10
It is preferably n-alkyl or n-alkoxy having C atoms, and also n-alkoxymethyl or n-alkoxyethyl having 1 to 8 C atoms.

R ¹ is methyl, ethyl, propyl, butyl,
Pentyl, hexyl, heptyl, octyl, nonyl, decyl, methoxy, ethoxy, propoxy, butoxy, pentoxy, hexosyl, heptoxy, octoxy, methoxymethyl, ethoxymethyl, propoxymethyl, butoxymethyl, methoxyethyl, ethoxyethyl or propoxyethyl Compounds of the formulas IfF3-1 to IfF3-8 are particularly highly preferred compounds. Z ¹¹ and Z ¹² in the compounds of formula IfF3-1~IfF3-8 is, -CH ₂ independently of each other in each case CH ₂ -, - COO-, a single bond or two or more of these bridges member Preference is given to combinations, in particular —CH ₂ CH ₂ — or a single bond.

The compound of the formula IfF is DE 3,102,017, JP
57 -140,747, DE3,233,641, DE2,93
7,911, EP 0,097,033, DE 3,509,26
0, DE3,732,284, DE3,928,783, EP0,
194,153, JP58-126,839, JP58-21
0,045, WO85 / 04874, DE3,315,29
5, EP0,193,191, JP63-280,063, DE
3,825,428, DE3,929,525, DE4,024,
760, DE 4,009,907, DE 4,007,040, DE
4,012,051, DE3,939,116, PCT / EP90
/ 00186, WO 90/08775, DE 3,929,76
4, DE4,004,650, DE4,013,854 and DE
It is preferably produced by the method described in 3,913,554.

A liquid crystal mixture containing one or more compounds of the formulas IfF2-1 to IfF2-4 and IfF3-1 to IfF3-8, wherein Phe. (F, 2) = Phe.3F or Phe.3F5F, has a dielectric constant. It is preferable because it has an advantageous value for the anisotropy Δε. Phe. (F, 2) = Phe.
3F or Phe.3F5F, wherein ring A13 or, if present, ring A14

[0243]

Embedded image A mixture containing compounds of the formulas IfF2-1 to IfF2-4 and IfF3-1 to IfF3-8, which are

(F) is Phe, Phe. 3F or Phe. 3F5F
Bicyclic compounds of the formulas IfF2-1 to IfF2-4 are particularly preferred. The bicyclic compounds of formulas IfF2-1 to IfF2-4, wherein Phe. (F) is Phe.2F, are characterized by good miscibility with other liquid crystals and are therefore particularly preferred. Liquid crystal mixtures containing these preferred compounds are preferred.

A liquid crystal mixture containing at least one of the following particularly preferred bicyclic compounds is more particularly preferred.

R ¹ -Cyc-Phe-F IfF2-1a R ¹ -Cyc-Phe. 2F-F IfF2-1b R ¹ -Cyc-Phe. 3F-F IfF2-1c R ¹ -Cyc-Phe. 3F5F-F IfF2-1d R ¹ -Cyc-CH ₂ CH ₂ -Phe-F IfF2-1e R ¹ -Cyc-CH ₂ CH ₂ -Phe. 2F-F IfF2-1f R ¹ -Cyc-CH ₂ CH ₂ -Phe. 3F -F IfF2-1g R ¹ -Cyc-CH ₂ CH ₂ -Phe.3F5F-F IfF2-1h R ¹ -Pyr-Phe-F IfF2-1i R ¹ -Pyr-Phe. 2F-F IfF2-1k R ^1- Pyr-Phe. 3F-F IfF2-1l R ¹ -Pyr-Phe. 3F5F-F IfF2-1m R ¹ -Pyd-Phe-F IfF2-1n R ¹ -Pyd-Phe. 2F-F IfF2-1o R ^1- Pyd-Phe. 3F-F IfF2-1p R ¹ -Pyd-Phe. 3F5F-F IfF2-1q R ¹ -Dio-Phe-F IfF2-1r R ¹ -Dio-Phe.2F-F IfF2-1s R ^1- Dio-Phe.3F-F IfF2-1t R ¹ -Dio-Phe.3F5F-F IfF2-1u R ¹ -Cyc-Phe-CF ₃ IfF2-2a R ¹ -Cyc-Phe.2F-CF ₃ IfF2-2b R ¹ -Cyc-Phe.3F-CF ₃ IfF2-2c R ¹ -Cyc-Phe.3F5F-CF ₃ IfF2-2d R ¹ -Cyc-CH ₂ CH ₂ -Phe-CF ₃ IfF2-2e R ¹ -Cyc-CH ₂ CH ₂ -Phe.2F-CF ₃ IfF2-2f R ¹ -Cyc-CH ₂ CH ₂ -Phe.3F-CF ₃ IfF2-2g R ¹ -Cyc-CH ₂ CH ₂ -Phe.3F5F-CF ₃ IfF2- 2h R ¹ -Pyr-Phe-CF ₃ IfF2-2i R ¹ -Pyr-Phe.2F-CF ₃ IfF2-2k R ¹ -Pyr-Phe.3F-CF ₃ IfF2-2l R ¹ -P yr-Phe.3F5F-CF ₃ IfF2-2m R ¹ -Pyd-Phe-CF ₃ IfF2-2n R ¹ -Pyd-Phe.2F-CF ₃ IfF2-2o R ¹ -Pyd-Phe.3F-CF ₃ IfF2- 2p R ¹ -Pyd-Phe.3F5F-CF ₃ IfF2-2q R ¹ -Dio-Phe-CF ₃ IfF2-2r R ¹ -Dio-Phe.2F-CF ₃ IfF2-2s R ¹ -Dio-Phe.3F- CF ₃ IfF2-2t R ¹ -Dio-Phe.3F5F-CF ₃ IfF2-2u R ¹ -Cyc-Phe-OCF ₃ IfF2-3a R ¹ -Cyc-Phe.2F-OCF ₃ IfF2-3b R ¹ -Cyc- Phe.3F-OCF ₃ IfF2-3c R ¹ -Cyc-Phe.3F5F-OCF ₃ IfF2-3d R ¹ -Cyc-CH ₂ CH ₂ -Phe-OCF ₃ IfF2-3e R ¹ -Cyc-CH ₂ CH _2- Phe.2F-OCF ₃ IfF2-3f R ¹ -Cyc-CH ₂ CH ₂ -Phe.3F-OCF ₃ IfF2-3g R ¹ -Cyc-CH ₂ CH ₂ -Phe.3F5F-OCF ₃ IfF2-3h R ^1- Pyr-Phe-OCF ₃ IfF2-3i R ¹ -Pyr-Phe.2F-OCF ₃ IfF2-3k R ¹ -Pyr-Phe.3F-OCF ₃ IfF2-3l R ¹ -Pyr-Phe.3F5F-OCF ₃ IfF2- 3m R ¹ -Pyd-Phe-OCF ₃ IfF2-3n R ¹ -Pyd-Phe.2F-OCF ₃ IfF2-3o R ¹ -Pyd-Phe.3F-OCF ₃ IfF2-3p R ¹ -Pyd-Phe.3F5F- OCF ₃ IfF2-3q R ¹ -Dio-Phe-OCF ₃ IfF2-3r R ¹ -Dio-Phe.2F-OCF ₃ IfF2-3s R ¹ -Dio-Phe.3F-OCF ₃ IfF2-3t R ¹ -Dio- Phe.3F5F-OCF ₃ IfF2-3u R ¹ -Cyc-Phe-OCHF ₂ IfF2-4a R ¹ -Cyc-Phe.2F-OCHF ₂ IfF2-4b R ¹ -Cyc-Phe.3F-OCHF ₂ IfF2-4c ^{R 1 -Cyc-Phe. 3F5F-} OCHF 2 IfF2-4d R 1 -Cyc-CH 2 CH 2 -Phe-OCHF 2 IfF2-4e R 1 -Cyc-CH 2 CH 2 -Phe. 2F-OCHF 2 IfF2-4f R ¹ -Cyc-CH ₂ CH ₂ -Phe.3F-OCHF ₂ IfF2-4g R ¹ -Cyc-CH ₂ CH ₂ -Phe.3F5F-OCHF ₂ IfF2-4h R ¹ -Pyr-Phe-OCHF ₂ IfF2-4i ^{R 1 -Pyr-Phe. 2F-} OCHF 2 IfF2-4k R 1 -Pyr-Phe. 3F-OCHF 2 IfF2-4l R 1 -Pyr-Phe. 3F5F-OCHF 2 IfF2-4m R 1 -Pyd-Phe-OCHF ₂ IfF2-4n R ¹ -Pyd-Phe.2F-OCHF ₂ IfF2-4o R ¹ -Pyd-Phe.3F-OCHF ₂ IfF2-4p R ¹ -Pyd-Phe.3F5F-OCHF ₂ IfF2-4q R ¹ -Dio -Phe-OCHF ₂ IfF2-4r R ¹ -Dio-Phe.2F-OCHF ₂ IfF2-4s R ¹ -Dio-Phe.3F-OCHF ₂ IfF2-4t R ¹ -Dio-Phe.3F5F-OCHF ₂ IfF2-4u The following small group of tricyclic compounds is more preferred.

R ¹ -Phe-Phe-Z ¹² -Phe. (F, 2) -F IfF3 -1a R ¹ -Phe-Phe-Z ¹² -Phe. (F, 2) -CF ₃ IfF3 -2a R ¹ -Phe-Phe-Z ¹² -Phe. (F, 2) -OCF ₃ IfF3 -3a R ¹ -Phe-Phe-Z ¹² -Phe. (F, 2) -OCHF ₂ IfF3 -4a R ¹ -Cyc-Phe -Z ¹² -Phe. (F, 2) -F IfF3 -1b R ¹ -Cyc-Phe-Z ¹² -Phe. (F, 2) -CF ₃ IfF3 -2b R ¹ -Cyc-Phe-Z ¹² -Phe (F, 2) -OCF ₃ IfF3 -3b R ¹ -Cyc-Phe-Z ¹² -Phe. (F, 2) -OCHF ₂ IfF3 -4b R ¹ -Cyc-Cyc-Z ¹² -Phe. 2) -F IfF3 -1c R ¹ -Cyc-Cyc-Z ¹² -Phe. (F, 2) -CF ₃ IfF3 -2c R ¹ -Cyc-Cyc-Z ¹² -Phe. (F, 2) -OCF ₃ IfF3 -3c R ¹ -Cyc-Cyc-Z ¹² -Phe. (F, 2) -OCHF ₂ IfF3 -4c R ¹ -Pyd-Phe-Z ¹² -Phe. (F, 2) -F IfF3 -1d R ¹ -Pyd-Phe-Z ¹² -Phe. (F, 2) -CF ₃ IfF3 -2d R ¹ -Pyd-Phe-Z ¹² -Phe. (F, 2) -OCF ₃ IfF3 -3d R ¹ -Pyd- ^{.. Phe-Z 12 -Phe (} F, 2) -OCHF 2 IfF3 -4d R 1 -Pyr-Phe-Z 12 -Phe (F, 2) -F IfF3 -1e R 1 -Pyr-Phe-Z 12 - Phe. (F, 2) -CF ₃ IfF3 -2e R ¹ -Pyr-Phe-Z ¹² -Phe. (F, 2) -OCF ₃ IfF3 -3e R ¹ -Pyr-Phe-Z ¹² -Phe. (F , 2) -OCHF ₂ IfF3 -4e R ¹ -Phe-Pyd-Z ¹² -Phe. (F, 2) -F IfF3 -1f R ¹ -Phe-Pyd-Z ¹² -Phe. (F, 2) -CF ₃ IfF3 -2f R ¹ -Phe-Pyd-Z ¹² -Phe. (F, 2) -OCF ₃ IfF3 -3f R ¹ -Phe-Pyd-Z ¹² -Phe. (F, 2) -OCHF ₂ IfF3 -4f R ¹ -Phe-Pyr-Z ¹² -Phe. (F, 2) -F IfF3 -1g R ¹ -Phe-Pyr-Z ¹² -Phe. (F, 2)- ^{_{.. CF 3 IfF3 -2g R 1}} -Phe-Pyr-Z 12 -Phe (F, 2) -OCF 3 IfF3 -3g R 1 -Phe-Pyr-Z 12 -Phe (F, 2) -OCHF 2 IfF3 - 4g R ¹ -Cyc-Dio-Z ¹² -Phe. (F, 2) -F IfF3 -1h R ¹ -Cyc-Dio-Z ¹² -Phe. (F, 2) -CF ₃ IfF3 -2h R ¹ -Cyc ^{.. -Dio-Z 12 -Phe (} F, 2) -OCF 3 IfF3 -3h R 1 -Cyc-Dio-Z 12 -Phe (F, 2) -OCHF 2 IfF3 -4h R 1 -Phe-Z 11 - Phe-Phe. (F, 2) -F IfF3 -5a R ¹ -Phe-Z ¹¹ -Phe-Phe. (F, 2) -CF ₃ IfF3 -6a R ¹ -Phe-Z ¹¹ -Phe-Phe. (F, 2) -OCF ₃ IfF3 -7a R ¹ -Phe-Z ¹¹ -Phe-Phe. (F, 2) -OCHF ₂ IfF3 -8a R ¹ -Cyc-Z ¹¹ -Phe-Phe. (F, 2) -F IfF3 -5b R ¹ -Cyc-Z ¹¹ -Phe-Phe. (F, 2) -CF ₃ IfF3 -6b R ¹ -Cyc-Z ¹¹ -Phe-Phe. (F, 2) -OCF ₃ IfF3- 7b R ¹ -Cyc-Z ¹¹ -Phe-Phe. (F, 2) -OCHF ₂ IfF3 -8b

In these compounds, Phe. (F, 2) is especially Phe, Phe. 3F or Phe. 3F5F. Z ¹² is -COO-
And the formula IfF3 -1a wherein Phe. (F, 2) is Phe.2F
Compounds of ~ 1h, 2a-2h, 3a-3h and 3a-3h and 4a-4h are more preferred. Z ¹² is —CH ₂ CH ₂ — or a single bond, and Phe. (F, 2) is Phe, Phe. 2F, Phe. 3F or
Formula I which is Phe.3F5F, especially Phe, Phe.3F and Phe.3F5F
Compounds of fF3-1a-1h, 2a-2h, 3a-3h and 4a-4h are more particularly preferred. Formulas IfF-5a, 6a, 7a, 8a, 5b, 6b,
In the compounds of 7b and 8b, Z ¹¹ is -CH ₂ CH ₂ -or -C
OO-, in particular -CH ₂ CH ₂ - and is preferably. Liquid crystal mixtures containing one or more of these preferred compounds have particularly advantageous properties.

A liquid crystal mixture containing at least one of the following preferred tricyclic compounds is more particularly preferred.

R ¹ -Phe-Phe-Phe-F IfF3-1a1 R ¹ -Phe-Phe-Phe. 2F-F IfF3-1a2 R ¹ -Phe-Phe-Phe. 3F-F IfF3-1a3 R ¹ -Phe -Phe-Phe.3F5F-F IfF3-1a4 R ¹ -Phe-Phe-Phe-CF ₃ IfF3-1a5 R ¹ -Phe-Phe-Phe.3F-CF ₃ IfF3-1a6 R ¹ -Phe-Phe-Phe- OCF ₃ IfF3-1a7 R ¹ -Phe-Phe-Phe.3F-OCF ₃ IfF3-1a8 R ¹ -Cyc-Phe-Phe-F IfF3-1b1 R ¹ -Cyc-Phe-Phe.2F-F IfF3-1b2 R ¹ -Cyc-Phe-Phe.3F-F IfF3-1b3 R ¹ -Cyc-Phe-Phe.3F5F-F IfF3-1b4 R ¹ -Cyc-Phe-Phe-CF ₃ IfF3-1b5 R ¹ -Cyc-Phe- Phe.3F-CF ₃ IfF3-1b6 R ¹ -Cyc-Phe-Phe-OCF ₃ IfF3-1b7 R ¹ -Cyc-Phe-Phe.3F-OCF ₃ IfF3-1b8 R ¹ -Cyc-Cyc-Phe-F IfF3 -1c1 R ¹ -Cyc-Cyc-Phe.2F-F IfF3-1c2 R ¹ -Cyc-Cyc-Phe.3F-F IfF3-1c3 R ¹ -Cyc-Cyc-Phe.3F5F-F IfF3-1c4 R ^1- Cyc-Cyc-Phe-CF ₃ IfF3-1c5 R ¹ -Cyc-Cyc-Phe.3F-CF ₃ IfF3-1c6 R ¹ -Cyc-Cyc-Phe-OCF ₃ IfF3-1c7 R ¹ -Cyc-Cyc -Phe. 3F-OCF ₃ IfF3-1c8 R ¹ -Pyd-Phe-Phe-F IfF3-1d1 R ¹ -Pyd-Phe-Phe.2F-F IfF3-1d2 R ¹ -Pyd-Phe-Phe.3F-F IfF3-1d3 R ¹ -Pyd-Phe-Phe.3F5F-F IfF3-1d4 R ¹ -Pyd-Phe-Phe-CF ₃ IfF3-1d5 R ¹ -Pyd-Phe-Phe.3F-CF ₃ IfF3-1d6 R ¹ -Pyd -Phe-Phe-OCF ₃ IfF3-1d7 R ¹ -Pyd-Phe-Phe.3F-OCF ₃ IfF3-1d8 R ¹ -Pyr-Phe-Phe-F IfF3-1e1 R ¹ -Pyr-Phe-Phe.2F- F IfF3-1e2 R ¹ -P yr-Phe-Phe.3F-F IfF3-1e3 R ¹ -Pyr-Phe-Phe.3F5F-F IfF3-1e4 R ¹ -Pyr-Phe-Phe-CF ₃ IfF3-1e5 R ¹ -Pyr-Phe-Phe.3F-CF ₃ IfF3-1e6 R ¹ -Pyr-Phe-Phe-OCF ₃ IfF3-1e7 R ¹ -Pyr-Phe-Phe.3F-OCF ₃ IfF3-1e8

Liquid crystal mixtures containing one or more compounds of the formula IfF, particularly preferred subformulas, have a wide mesogenic range,
It is characterized by a relatively high clearing point, advantageous values for birefringence and flow viscosity, low miscibility with the polymer used for the matrix, and especially advantageous values for dielectric anisotropy and high UV and temperature stability.

The liquid crystal mixture is 1 to 40%, particularly 5 to 30%
Of the formula IfF, especially preferred sub-formulae. In this case, the liquid crystal mixture has 1 to 5 kinds, particularly 1 to 5 kinds.
It preferably comprises three compounds of the formula IfF, particularly preferred subformulae.

Formulas IfF, especially formulas IfF2-1 to IfF2-4 and IfF3-
1-IfF3-8, more particularly one or more compounds selected from the group of compounds of the preferred sub-formula, and furthermore formulas II1-II2
A mixture containing at least one compound selected from the group consisting of 8, III1 to III3 and V1 to VI8 is a particularly preferred liquid crystal mixture. In the liquid-crystal mixtures used according to the invention, the compounds of the formula IfF, in particular the compounds IfF2 and IfF3, more particularly at least one compound of the preferred sub-formula, and additionally the compounds of the formula II1
To II28, III1 to III3 and at least one compound of IV1 to IV8 has a mass of 15% to 100%
%, Especially 25% to 100%.

Liquid-crystal mixtures based on the following component mixtures, each containing at least one compound from the substance groups indicated in each case, are particularly suitable for application in matrix systems, but in particular in liquid-crystal mixtures: If the mass of the formula IfF of formula (I), especially preferred sub-formulas or other terminally fluorinated compounds, is less than 10%, especially less than 5%, they are less suitable for network systems.

[0255]

[Table 18]

On the other hand, a liquid crystal mixture containing this kind of component mixture has the formula contained in these component mixtures.
IfF, especially preferred compounds of the sub-formula or other terminally fluorinated compounds have a mass of more than 5%, especially 10%
Larger, more particularly 12.5% or more, is generally preferred for application to network systems.
One of the above component mixtures and additionally the compounds Ia, Ic, Id, I
Liquid crystal mixtures containing e, IfCl. F, Ig, Ih or Ii, one or more compounds selected from the group of compounds of the particularly preferred sub-formula, are also preferred for application in both matrix and network systems . In these mixtures,
The mass of the terminally fluorinated compound can be less than 5%. U = —CF ₂ , —OCF ₂ or —OCHF and at least one compound of the formula IfF, and additionally formulas II1 to II28, III1 to III
Liquid crystal mixtures containing 3 and at least one compound selected from the group of compounds IV1 to IV8 are also preferred for application to both matrix and network systems.

Furthermore, the following component mixtures, each containing at least one compound from the indicated substance group, are suitable for both matrix systems and network systems.

[0258]

[Table 19]

[0259]

[Table 20]

[0260]

[Table 21]

Preference is given to liquid-crystal mixtures based on the following component mixtures T (IfF) 30 to 35, each containing at least one compound from the compounds of the formulas mentioned in each case. The following table further shows the preferred masses of these compounds in the component mixture. The component mixture is 2 to 38 types,
It preferably contains 2 to 35, especially 2 to 25 compounds. The sum of the masses of these compounds in the component mixture is 100%. The mass of the component mixture in the liquid crystals according to the invention is between 10% and 100%, in particular between 15% and 100%, more particularly between 25% and 100%.

[0262]

[Table 22] @ 079 The compound in which T2 is Cl and v is 0

[0263]

Embedded image (Where R ¹ has the meaning described above) is a more preferred formula
It is a compound of If.

The compounds of the formula IfCl have the lower formulas IfCl2-1 to IfCl2-8
And the following preferred bicyclic and tricyclic compounds of IfCl3-1 to IfCl3-47.

R ¹ -Phe-Phe-Cl IfCl2-1 R ¹ -Pyr-Phe-Cl IfCl2-2 R ¹ -Cyc-Phe-Cl IfCl2-3 R ¹ -Phe-C≡C-Phe-Cl IfCl2- 4 R ¹ -Phe-COO-Phe-Cl IfCl2-5 R ¹ -Phe-OOC-Phe-Cl IfCl2-6 R ¹ -Pyd-Phe-Cl IfCl2-7 R ¹ -Cyc-COO-Phe-Cl IfCl2- 8 R ¹ -Phe-Phe-Phe-Cl IfCl3-1 R ¹ -Cyc-Phe-Phe-Cl IfCl3-2 R ¹ -Cyc-Cyc-Phe-Cl IfCl3-3 R ¹ -Phe-Cyc-Phe-Cl IfCl3-4 R ¹ -Phe-CH ₂ CH ₂ -Phe-Phe-Cl IfCl3-5 R ¹ -Phe-COO-Phe-Phe-Cl IfCl3-6 R ¹ -Phe-Phe-CH ₂ CH ₂ -Phe- Cl IfCl3-7 R ¹ -Phe-Phe-COO-Phe-Cl IfCl3-8 R ¹ -Phe-Phe-OOC-Phe-Cl IfCl3-9 R ¹ -Cyc-CH ₂ CH ₂ -Phe-Phe-Cl IfCl3 -10 R ¹ -Cyc-COO-Phe-Phe-Cl IfCl3-11 R ¹ -Cyc-Phe-CH ₂ CH ₂ -Cl IfCl3-12 R ¹ -Cyc-Phe-C≡C-Phe-Cl IfCl3-13 R ¹ -Cyc-CH ₂ CH ₂ -Phe-C≡C-Phe-Cl IfCl3-14 R ¹ -Cyc-Phe-COO-Phe-Cl IfCl3-15 R ¹ -Cyc-Phe-OOC-Phe-Cl IfCl3 -16 R ¹ -Cyc-CH ₂ CH ₂ -Phe-COO-Phe-Cl IfCl3-17 R ¹ -Phe-Cyc-COO-Phe-Cl IfCl3-18 R ¹ -Phe-COO-Cyc-Phe-Cl IfCl3 -19 R ¹ -Phe-OOC-Cyc-Phe-Cl IfCl3 -20 R ¹ -Cyc- Cyc-CH ₂ CH ₂ -Phe-Cl IfCl3 -21 R ¹ --Cyc- Cyc-COO-Phe-Cl IfCl3- 22 R ^1- Cyc- Cyc-OOC-Phe-Cl IfCl3 -23 R ¹ -Cyc-CH ₂ CH ₂ -Cyc-COO-Phe-Cl IfCl3 -24 R ¹ -Cyc- CH ₂ CH ₂ -Cyc- Phe-Cl IfCl3-25 R ¹ -Cyc-COO-Cyc-Phe-Cl IfCl3 -26 R ¹ -Cyc-OOC-Cyc-Phe-Cl IfCl3-27 R ¹ -Phe-COO- Phe-COO -Phe-Cl IfCl3-28 R ^1- Phe-COO- Phe-OOC -Phe-Cl IfCl3-29 R ¹ -Phe-OOC- Phe-COO -Phe-Cl IfCl3-30 R ¹ -Phe-OOC- Phe-OOC-Phe-Cl IfCl3-31 R ¹ -Cyc-COO- Phe-COO -Phe-Cl IfCl3-32 R ¹ -Cyc-COO- Phe-OOC -Phe-Cl IfCl3-33 R ¹ -Cyc-OOC- Phe-OOC -Phe-Cl IfCl3-34 R ¹ -Cyc-OOC- Phe-COO-Phe-Cl IfCl3-35 R ¹ -Cyc-COO- Cyc-COO -Phe-Cl IfCl3-36 R ¹ -Cyc-OOC- Cyc-COO-Phe-Cl IfCl3-37 R ¹ -Cyc-COO- Cyc-OOC -Phe-Cl IfCl3-38 R ¹ -Cyc-OOC- Cyc-OOC -Phe-Cl IfCl3-39 R ¹ -Pyr-Phe-Phe-Cl IfCl340 R ¹ -Pyd- Phe-Phe-Cl IfCl3-41 R ¹ -Phe-Pyr-Phe-Cl IfCl3-42 R ¹ -Phe-Pyd-Phe-Cl IfCl3-43 R ¹ -Cyc-Pyr-Phe-Cl IfCl3-44 R ^1- Cyc-Pyd-Phe-Cl IfCl3-45 R ¹ -Pyr-CH ₂ CH ₂ -Phe-Phe-Cl IfCl3-46 R ¹ -Pyd-Ch ₂ CH ₂ -Phe-Phe-Cl IfCl3-47

In compounds of formulas IfCl2 and IfCl3, R
¹ is preferably a linear group, preferably an alkyl, alkenyl or alkoxy having 1 to 10, especially 1 to 8 C atoms. n-alkoxyalkyl compounds,
Particularly preferred are n-alkoxymethyl and n-alkoxyethyl compounds.

R ¹ -Phe-Phe-Cl IfCl2-1 R ¹ -Pyr-Phe-Cl IfCl2-2 R ¹ -Cyc-Phe-Cl IfCl2-3 R ¹ -Phe-C≡C-Phe-Cl IfCl2- 4 R ¹ -Phe-COO-Phe-Cl IfCl2-5 R ¹ -Phe-OOC-Phe-Cl IfCl2-6 R ¹ -Pyd-Phe-Cl IfCl2-7 R ¹ -Cyc-COO-Phe-Cl IfCl2- 8 R ¹ -Phe-Phe-Phe-Cl IfCl3-1 R ¹ -Cyc-Phe-Phe-Cl IfCl3-2 R ¹ -Cyc-Cyc-Phe-Cl IfCl3-3 R ¹ -Phe-Cyc-Phe-Cl IfCl3-4 R ¹ -Phe-CH ₂ CH ₂ -Phe-Phe-Cl IfCl3-5 R ¹ -Phe-COO-Phe-Phe-Cl IfCl3-6 R ¹ -Phe-Phe- CH ₂ CH ₂ -Phe- Cl IfCl3-7 R ¹ -Phe-Phe-COO-Phe-Cl IfCl3-8 R ¹ -Phe-Phe-OOC-Phe-Cl IfCl3-9 R ¹ -Cyc- CH ₂ CH ₂ -Phe-Phe-Cl IfCl3 -10 R ¹ -Cyc-COO-Phe-Phe-Cl IfCl3-11 R ¹ --Cyc- Phe- CH ₂ CH ₂ -Cl IfCl3-12 R ¹ -Cyc- Phe- C≡C-Phe-Cl IfCl3 -13 R ¹ -Cyc-CH ₂ CH ₂ -Phe- C≡C-Phe-Cl IfCl3-14 R ¹ -Cyc- Ph-COO-Phe- Cl IfCl3-15 R ¹ -Cyc- Phe-OOC-Phe- Cl IfCl3-16 R ¹ -Cyc- CH ₂ CH ₂ -Phe-COO-Phe-Cl IfCl3-17 R ¹ -Phe-Cyc-COO-Phe- Cl IfCl3 -18 R ¹ -Phe-COO-Cyc-Phe- Cl IfCl3 -19 R ¹ -Phe-OOC-Cyc-Phe-Cl IfCl3 -20 R ¹ -Cyc- Cyc-CH ₂ CH ₂ -Phe-Cl IfCl3 -21 R ¹ --Cyc- Cyc-COO-Phe- Cl IfCl3 -22 R ¹ -Cyc- Cyc-OOC-Phe-Cl IfCl3 -23 R ¹ -Cyc- CH ₂ CH ₂ -Cyc-COO-Phe-Cl IfCl3-24 R ¹ -Cyc- CH ₂ CH ₂ -Cyc -Phe-Cl IfCl3-25 R ¹ -Cyc-COO-Cyc-Phe-Cl IfCl3 -26 R ¹ -Cyc-OOC-Cyc-Phe-Cl IfCl3-27 R ¹ -Phe-COO- Phe-COO -Phe- Cl IfCl3-28 R ¹ -Phe-COO- Phe-OOC -Phe-Cl IfCl3-29 R ¹ -Phe-OOC- Phe-COO -Phe-Cl IfCl3-30 R ¹ -Phe-OOC- Phe-OOC-Phe -Cl IfCl3-31 R ¹ -Cyc-COO- Phe-COO -Phe-Cl IfCl3-32 R ¹ -Cyc-COO- Phe-OOC -Phe-Cl IfCl3-33 R ¹ -Cyc-OOC- Phe-OOC- Phe-Cl IfCl3-34 R ¹ -Cyc-OOC- Phe-COO-Phe-Cl IfCl3-35 R ¹ -Cyc-COO- Cyc-COO -Phe-Cl IfCl3-36 R ¹ -Cyc-OOC- Cyc-COO -Phe-Cl IfCl3-37 R ¹ -Cyc-COO- Cyc-OOC -Phe-Cl IfCl3-38 R ¹ -Cyc-OOC- Cyc-OOC -Phe-Cl IfCl3-39 R ¹ -Pyr-Phe-PheCl IfCl340 R ¹ -Pyd-Phe-Phe-Cl IfCl3-41 R ¹ -Phe-Pyr-Phe-Cl IfCl3-42 R ¹ -Phe-Pyd-Phe-Cl IfCl3-43 R ¹ -Cyc-Pyr-Phe-Cl IfCl3 -44 R ¹ -Cyc-Pyd-Phe-Cl IfCl3-45 R ¹ -Pyr-CH ₂ CH ₂ -Phe-Phe-Cl IfCl3-46 R ¹ -Pyd-Ch ₂ CH ₂ -Phe-Phe-Cl IfCl3- 47

In compounds of formulas IfCl2 and IfCl3, R
¹ is preferably a linear group, preferably an alkyl, alkenyl or alkoxy having 1 to 10, especially 1 to 8 C atoms. n-alkoxyalkyl compounds,
Particularly preferred are n-alkoxymethyl and n-alkoxyethyl compounds.

R ¹ is methyl, ethyl, propyl, butyl,
Bentil, hexyl, heptyl, octyl, nonyl, decyl, methoxy, ethoxy, butoxy, pentoxy, hexosyl, heptoxy, octoxy, methoxymethyl,
Ethoxymethyl, propoxymethyl, butoxymethyl,
Formulas IfCl2-1 to IfCl2-8 and IfCl3-1 to IfCl3-47 which are methoxyethyl, ethoxyethyl or propoxyethyl
Are particularly highly preferred compounds.

Formula IfCl and preferred subformulas IfCl2-2 to IfC
The compounds l2-8 and IfCl3-1 to IfCl3-37 are mostly known, for example JP60 / 260679A2; JP5
9/81375 A2; EP 0,123,907; JP58 / 7
9938A2; DE 3,136,624; Marsate (Ma
lthete), Mol. Cryst. Liq. Cryst. 23 , 233 (197
3); Marsate et al., J. Phys. Colloq., 37, C31 (1
976); JP Vanmeter, etc., Mol. Cryst. L
iq. Cryst., 22 , 271 (1973); ME Newbert (Neub
ert) et al., Mol. Cryst. Liq. Cryst., 135 , 283 (1986);
JP / 56 / 120641A2; EP 152,014; DE3,
139,130; HJ Muller et al., Mol. Cryst.
Liq. Cryst., 92 , 63 (1983); JP61 / 225147A.
2: JP57 / 183727A2: DE 3,139,130;
GW Gray (Gray) and JW Goodby (Goodby), Mo
l. Cryst. Liq. Cryst., 37 , 157 (1976); JP57 /
18538A2; Takatsu et al., Mol. Cryst.
Liq. Cryst., 100 345 (1983); DE 3,233,64.
1: GB 2,071,1131; SM Kelly and
Hp. Sshad, Helv. Chim. Acta, 68 , 1444.
(1985); USP 4,726,910; R. Dabroski (Dabro
wski) et al., Moll Cryst. Liq. Crysyt. 107 , 411 (1984);
JP56 / 120641A2; JP57 / 31645A2; J
P60 / 41638A2; JP 59 / 29640A2; DE3,
317,507; GB 2,070,593; JP57 / 541
48A2; H. Takatsu et al., Mol. Cryst. Liq. Cryst., 10
8 , 157 (1984); JP59 / 113081A2; EP10.
2,047 ,; JP. Banmeter, Mol.Cryst. Liq. C
ryst., 22 , 285 (1973); H.-J. Deutsche
r) et al., J. Prakt. Chem., 321 , 47 (1979); H.-J. Deitcher et al., J. Parkt. Chem., 321 , 969 (1979); JP
58 / 4745A2.

Compounds of formula IfCl1, especially compounds of formulas IfCl2-1 to IfCl2-
Liquid crystal mixtures containing one or more compounds selected from the group of preferred compounds of 8 and IfCl3-1 to IfCl3-47 are advantageous values for birefringence Δn and dielectric anisotropy, high stability, relatively simple It is characterized by manufacturability, low miscibility with the polymers used for the matrix, and especially advantageous values for the wide mesogenic range, relatively high clearing points and the temperature dependence of the flow viscosities and electro-optical parameters.

The liquid crystal mixture of the present invention comprises 1 to 40%, especially 5%
It preferably contains 〜30% of the compounds of the formula IfCl, particularly the preferred subformulae. In this case, the liquid crystal mixture has the formula IfCl,
It is preferred to contain from 1 to 5 and especially from 1 to 3 compounds of the particularly preferred sub-formula.

Formulas IfCl, especially Formulas IfCl2-1 to IfCl2-8 and If
One or more compounds selected from the group of compounds Cl3-1 to IfCl3-47 and further formulas II1-II28, III1-III3 and IV1-IV
A mixture containing at least one compound selected from the group consisting of eight compounds is a particularly preferred liquid crystal mixture. In the liquid-crystal mixtures used according to the invention, the compounds of the formula IfCl, particularly preferred at least one compound of the sub-formula, and also the compounds of the formulas II1 to II2
8, the mass of the component mixture comprising at least one of the compounds III1 to III3 and IV1 to IV8 is preferably from 15% to 100%, particularly preferably from 25% to 100%.

Mixtures containing at least one compound from Group C below and at least one compound from Group D below are particularly preferred liquid crystal mixtures.

[0275]

[Table 23]

Preference is given to liquid-crystal mixtures based on the following component mixtures T (ICl) 1 to 3, each containing at least one compound from the compounds of the formulas mentioned in each case. The following table further shows the preferred masses of these compounds in the component mixture. The component mixture contains 2 to 38, preferably 2 to 35, especially 2 to 25 compounds. The sum of the masses of these compounds in the component mixture is 10
0%. The mass of the component mixture in the liquid crystal of the present invention is 10
% To 100%, especially between 15% and 100%, more particularly between 25% and 100%.

[0277]

[Table 24]

[0278]

Embedded image Is a compound of formula If is Phe.3F-Cl or Phe.3F5F

[0279]

Embedded image (Where R ¹ is as defined above, and X ⁷ is F or H
Is a more preferred compound.

[0280]

Embedded image And bicyclic and tricyclic compounds.

In the bicyclic compound of the formula IfCl.F2, the ring A ¹³
Is Phe, Phe.F, Cyc, Pyr, Pyd or Dio, especially Phe, Cyc,
Preferably it is Pyd or Dio. Z ¹¹ is a single bond, -COO
-, -OCO- or -CH ₂ CH ₂ -, in particular a single bond, -CH ₂ CH ₂ - or -COO-.

Particular preference is given to the following subgroups of bicyclic compounds of the formulas IfCl.F2-1 to IfCl.F2-19.

R ¹ -Phe-Phe.3F-Cl IfCl.F2-1 R ¹ -Phe-.3F-Phe.3F-Cl IfCl.F2-2 R ¹ -Cyc-Phe.3F-Cl IfCl.F2- 3 R ¹ -Pyr-Phe.3F-Cl IfCl.F2-4 R ¹ -Pyd-Phe.3F-Cl IfCl.F2-5 R ¹ -Dio-Phe.3F-Cl IfCl.F2-6 R ¹ -Phe -CH ₂ CH ₂ -Phe.3F-Cl IfCl.F2-7 R ¹ -Phe-COO-Phe.3F-Cl IfCl.F2-8 R ¹ -Cyc-CH ₂ CH ₂ -Phe.3F-Cl IfCl. F2-9 R ¹ -Cyc-COO-Phe.3F-Cl IfCl.F2-10 R ¹ -Cyc-OCO-Phe.3F-Cl IfCl.F2-11 R ¹ -Phe-Phe.3F5F-Cl IfCl.F2 -12 R ¹ -Cyc-Phe.3F5F-Cl IfCl.F2-13 R ¹ -Pyr-Phe.3F5F-Cl IfCl.F2-14 R ¹ -Pyd-Phe.3F5F-Cl IfCl.F2-15 R ^1- Dio-Phe.3F5F-Cl IfCl.F2-16 R ¹ -Phe-CH ₂ CH ₂ -Phe.3F5F-Cl IfCl.F2-17 R ¹ -Phe-COO-Phe.3F5F-Cl IfCl.F2-18 R ¹ -Cyc-CH ₂ CH ₂ -Phe.3F5F-Cl IfCl.F2-19 In a tricyclic compound of the formula IfCl.F3, Z ¹¹ and Z ¹² are
A single bond independently of one another, -COO-, -COC- or -CH ₂ CH ₂
And one of the bridging radicals Z ¹¹ and Z ¹² is preferably a single bond.

Ring A ¹³ and ring A ¹⁴ are independently of each other Phe,
It is preferably Phe.F, Cyc, Pyr, Pyd or Dio,
If one of the rings A ¹³ and ring A ¹⁴ is a heterocyclic compound, the other ring is Phe, Phe.F or Cyc, is preferably particularly Ph e or Cyc.

The following subgroups of tricyclic compounds of the formulas IfCl.F3-1 to IfCl.F3-38 are particularly preferred.

R ¹ -Phe-Phe.F-Phe.3F-Cl IfCl.F3-1 R ¹ -Phe-Phe-Phe.3F-Cl IfCl.F3-2 R ¹ -Cyc-Phe-Phe.F- Phe.3F-Cl IfCl.F3-3 R ¹ -Cyc-Cyc-Phe.3F-Cl IfCl.F3-4 R ¹ -Phe-Pyr-Phe.3F-Cl IfCl.F3-5 R ¹ -Phe-Pyd -Phe.3F-Cl IfCl.F3-6 R ¹ -Dio-Cyc-Phe.3F-Cl IfCl.F3-7 R ¹ -Dio-Phe-Phe.3F-Cl IfCl.F3-8 R ¹ -Pyr- Phe-Phe.3F-Cl IfCl.F3-9 R ¹ -Pyd-Phe-Phe.3F-Cl IfCl.F3-10 R ¹ -Cyc-Pyr-Phe.3F-Cl IfCl.F3-11 R ¹ -Cyc -Pyd-Phe.3F-Cl IfCl.F3-12 R ¹ -Phe.F-Pyd-Phe.3F-Cl IfCl.F3-13 R ¹ -Pyd-Phe.F-Phe.3F-Cl IfCl.F3- 14 R ¹ -Cyc-CH ₂ CH ₂ -Phe-Phe.3F-Cl IfCl.F3-15 R ¹ -Cyc-Cyc-CH ₂ CH ₂ -Phe.3F-Cl IfCl.F3-16 R ¹ -Dio- Cyc-CH ₂ CH ₂ -Phe.3F-Cl IfCl.F3-17 R ¹ -Dio-Phe-CH ₂ CH ₂ -Phe.3F-Cl IfCl.F3-18 R ¹ -Phe-Phe.F-CH ₂ CH ₂ -Phe.3F-Cl IfCl.F3-19 R ¹ -Phe-COO-Phe.F-Phe.3F-Cl IfCl.F3-20 R ¹ -Phe-COO-Phe-COO-Phe.3F-Cl IfCl.F3-21 R ¹ -Cyc-COO-Phe-Phe.3F-Cl IfCl.F3-22 R ¹ -Cyc-Phe-COO-Phe.3F-Cl IfCl.F3-23 R ¹ -Cyc-COO- Cyc-Phe.3F-Cl IfCl.F3-24 R ¹ -CyC-Cyc-COO-Phe.3F-Cl IfCl.F3-25 R ¹ -Phe-Phe-Phe.3F5F-Cl IfCl.F3-26 R ¹ - Cyc-Phe-Phe.3F5F-Cl IfCl.F3-27 R ¹ -Cyc-Cyc-Phe.3F5F-Cl IfCl.F3-28 R ¹ -Pyr-Phe-Phe.3F5F-Cl IfCl.F3-29 R ¹ -Pyd-Phe-Phe.3F5F-Cl IfCl.F3-30 R ¹ -Phe-Pyr-Phe.3F5F-Cl IfCl.F3-31 R ¹ -Phe-Pyd-Phe.3F5F-Cl IfCl.F3-32 R ¹ -Doi-Phe-Phe.3F5F-Cl IfCl.F3-33 R ¹ -Cyc-CH ₂ CH ₂ -Phe-Phe.3F5F-Cl IfCl.F3-34 R ¹ -Cyc-Cyc-CH ₂ CH ₂ -Phe.3F5F-Cl IfCl.F3-35 R ¹ -Phe-Phe-COO-Phe.3F5F-Cl IfCl.F3-36 R ¹ -Cyc-COO-Phe.3F5F-Cl IfCl.F3-37 R ^1- Cyc-CyC-COO-Phe.3F5F-Cl IfCl.F3-38

Formula IfCl.F, particularly preferred subformula IfCl.F2-1
In the compounds of -IfCl.2-19 and IfCl.3-1 to IfCl.F3-38, R1 is preferably alkyl, alkoxy, alkoxyalkyl and alkenyl having ¹ to 10 C atoms.

R ¹ is methyl, ethyl, propyl, butyl,
It is preferably pentyl, hexyl, heptyl, octyl, nonyl, decyl, methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, heptoxy, octoxy, nonyloxy, decyloxy, methoxyethyl, ethoxyethyl, or propoxyethyl.

The compounds of formulas IfCl.F2 and IfCl.F3 are DE3,
Preferably, it is prepared by the method described in US Pat.

Formulas IfCl.F, especially Formulas IfCl.F2-1 to IfCl.F2-19
And a liquid crystal mixture containing one or more compounds selected from the group of compounds of IfCl.F3-1 to IfCl.F3-38 is birefringent,
It is characterized by advantageous values for clearing point and viscosity, and especially for Δε, high UV and temperature stability and high resistivity. These mixtures are preferred.

These liquid crystal mixtures have a content of 1 to 40%, especially 5%.
It preferably contains 〜30% of the compound of the formula IfCl.F, particularly preferred subformulae. In this case, the liquid crystal mixture has the formula IfC
It preferably contains 1F, particularly preferred 1 to 5, especially 1 to 3, sub-compounds.

Those skilled in the art will recognize, without inventive assistance, a limited group of compounds of the formula IfCl.F so that the liquid crystals and the filled electro-optics are optimized within certain limits for particular applications. In particular, the formulas IfCl.F2-1 to IfCl.F2-9 and IfCl.F3-1 to I
It can always be selected from a small group of compounds fCl.3-1 to IfCl.F3-38. If it is desired that the liquid crystal mixture has a high or even very high birefringence, for example,
For example, IfCl.F2-1, IfCl.F2-2, IfCl.F2-4, IfCl.F2-
5, IfCl.F2-7, IfCl.F2-8, IfCl.F2-12, IfCl.F2-1
4, IfCl.F2-15, IfCl.F2-17, IfCl.F2-18, IfCl.F3
-1, IfCl.F3-2, IfCl.F3-5, IfCl.F3-6, IfCl.F3-
9, IfCl.F3-10, IfCl.F3-13, IfCl.F3-14, IfCl.F3-
19, IfCl.F3-20, IfCl.F3-21, IfCl.F3-26, IfCl.F3
-29, IfCl.F3-30, IfCl.F31, IfCl.F3-32 and IfCl.
It is preferred to choose a compound of the formula IfCl.F, which does not have a saturated ring system such as F3-36, a particularly preferred sub-formula.

Furthermore, for example, in order for the mixture to have a relatively high or high Δε, compounds having a pyridine or pyrimidine ring and / or a Phe.3F5F-Cl group can be advantageously used.

Compounds of formula IfCl.F, especially compounds of formulas IfCl.F2-1 to IfC.
l.F2-19 and one or more compounds selected from the group of preferred compounds of IfCl.F3-1 to IfCl.F3-38 and further compounds
A mixture containing at least one compound selected from the group consisting of II1 to II27, III1 to III3 and IV1 to IV8 is a particularly preferred liquid crystal mixture.

In the liquid-crystal mixtures used according to the invention, from the compounds IfCl.F, at least one compound of the particularly preferred sub-formula, and at least one compound of the formulas II1-II27, III1-III3 and IV1-IV8 The weight of the resulting component mixture is preferably between 15% and 100%, in particular between 25% and 100%.

The following component mixture T (IfCl.2) containing at least one compound of each of the indicated compound groups:
F) is particularly preferred and is suitable for application in both matrix and network systems.

[0297]

[Table 25]

[0298]

[Table 26]

In addition to the dielectrically positive component A consisting of a dielectrically positive compound of Δε> 2, a dielectrically neutral component B consisting of a compound of −2 ≦ Δε ≦ + 2 and, if necessary, Δε <-2
Further preferred is a liquid crystal mixture containing a dielectrically negative component C consisting of

Assuming that the mass of the dielectrically positive compound in the liquid crystal is a, the mass of the dielectrically neutral compound is b, and the mass of the dielectrically negative compound is c, a is ≧ 30.
%, Especially> 50%. When the dielectrically positive component A is based on carbonitrile in particular, the liquid crystal has a dielectrically neutral component to suppress the formation of a dimer having an antiparallel correlated dipole moment. It is preferred to include. The value obtained by dividing the mass of the dielectrically positive component by the mass of the dielectrically neutral component is 35 ≧ a / b ≧ 0.5, especially 15
Oh Ru is preferably at ≧ a / b ≧ 1.

On the other hand, the liquid crystal has F, Cl, C as polar terminal groups.
When the main component is a liquid crystal compound having F ₃ , OCF ₃ , OCHF ₂ or NCS, the content of a dielectrically neutral compound may be small or zero. b is preferably ≦ 45%, particularly ≦ 35%, and more particularly ≦ 25%.

The content of dielectrically negative compounds is generally low, as low switching voltages are usually desirable. c is ≦ 10
%. Particularly preferred is ≦ 5%, and liquid crystal mixtures with c ≦ 3% are generally particularly preferred.

Formula Ig R ¹ -Q ⁴ -COO-Q ⁵ -R ² Ig wherein Q ⁴ and Q ⁵ are each independently of the other

[0304]

Embedded image And one of Q ⁴ and Q ⁵ is

[0305]

Embedded image And R ¹ and R ² independently of one another in each case have the meaning given for R ¹ in claim 1). preferable.

The compounds of the formula Ig are preferably of the following formulas Ig2-1 and I
g2-2 bicyclic compound. R ¹ -Phe-COO-Phe-R ² Ig2-1 R ¹ -Cyc-COO-Phe-R ² Ig2-2

In the compounds of the formulas Ig2-1 and Ig2-2, R ¹
And R ² are, independently of one another, preferably alkyl or alkoxy having 1 to 10, in particular 1 to 8 C atoms, furthermore also n-alkoxyalkyl, especially n-alkoxymethyl and n-alkoxyethyl . Formula Ig2-
One of the two 2,4-phenylene groups of the compound of formula I
The 1,4-phenylene group of the compound of -2 can be substituted at two or three positions by Cl or F, especially by F at three positions.

Particularly preferred compounds are those of the following formula:

R ¹ -Phe-COO-Phe-alkyl or alkoxy Ig2-1a R ¹ -Phe-COO-Phe.3F-alkyl or alkoxy Ig2-1b R ¹ -Phe-COO-Phe.2F-alkyl or alkoxy Ig2 -1c R ¹ -Phe-COO-Phe.3F-Alkoxymethyl Ig2-1d R ¹ -Cyc-COO-Phe-alkyl or alkoxy Ig2-2a R ¹ -Cyc-COO-Phe.2F-Alkyl or alkoxy Ig2-2b R ¹ -Cyc-COO-Phe.3F-alkyl or alkoxy Ig2-2c Compounds of the formula Ig are those in which one of the groups Q ⁴ and Q ⁵ is 1,4-phenylene or trans-1,4-cyclohexylene, But

[0310]

Embedded image Embedded image

R ¹ -Phe-COO-Phe. (F) -Phe.R ² Ig3-1 R ¹ -Phe-Phe-COO-Phe. (F) .R ² Ig3-2 R ¹ -Cyc-Phe. (F) -COO-Phe. (F) -R ² Ig3-3 R ¹ -Cyc-COO-Phe-COO-Phe. (F) -R ² Ig3-4 R ¹ -Phe-COO-Phe. (F ) -COO-Phe-R ² Ig3-5 R ¹ -Cyc-Cyc-COO-Phe. (F) -R ² Ig3-6 R ¹ -Phe-COO-Cyc-Cyc-R ² Ig3-7 R ^1- Cyc-COO-Phe-Cyc-R ² Ig3-8 R ¹ -Cyc-COO-Phe. (F) -Phe-R ² Ig3-9 R ¹ -Phe. (F) -Phe-COO-Cyc-R ² Ig3-10

In the compounds of the subformulae Ig3-1 to Ig3-10, R
¹ and R ² are preferably, independently of one another, n-alkyl or n-alkoxy having 1 to 10 C atoms,
Also n-alkoxymethyl and n-alkoxyethyl having 1 to 8 C atoms. Compounds of formula Ig3-1 to Ig3-10 can have one of the 1,4-phenylene groups laterally monosubstituted by X = F or Cl. In this case, it is preferred that three sites be replaced by F.

R ¹ and R ² independently of one another are methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, methoxymethyl, ethoxymethyl, propoxymethyl , Butoxymethyl, pentoxymethyl, methoxyethyl, ethoxyethyl, propoxyethyl, butoxyethyl, or pentoxyethyl of the formula Ig3-1, Ig3-2, Ig3-3, Ig3-5, Ig3-6, Ig3-
8, laterally unsubstituted or monosubstituted compounds of Ig3-9 and Ig3-10 are particularly preferred.

The compounds of the formula Ig are such that the radicals Q ⁴ and Q ⁵ are in each case independently of one another

[0315]

Embedded image Embedded image

Preferred compounds are those of the following formulas Ig4-1 to Ig4-10.

R ¹ -Phe-Phe-COO-Phe. (F) -Phe-R ² Ig4-1 R ¹ -Phe. (F) -Phe-COO-Cyc-Phe-R ² Ig4-2 R ^1- Phe-Phe. (F) -COO-Phe-COO-Phe-R ² Ig4-3 R ¹ -Phe-Phe. (F) -COO-Cyc-Cyc-R ² Ig4-4 R ¹ -Cyc-Phe- COO-Phe. (F) -Phe-R ² Ig4-5 R ¹ -Cyc-Phe-COO-Phe. (F) -COO-Phe. (F) -R ² Ig4-6 R ¹ -Cyc-Phe- COO-Cyc-Cyc-R ² Ig4-7 R ¹ -Cyc-Phe. (F) -COO-Phe-Cyc-R ² Ig4-8 R ¹ -Cyc-Cyc-COO-Phe-Cyc-R ² Ig4- 9 R ¹ -Cyc-COO-Phe-COO-Phe. (F) -Phe-R ² Ig4-10

In the compounds of the formulas Ig4-1 to Ig4-10, R ¹ and R ² independently of one another are methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, methoxy, ethoxy, propoxy , Butoxy, pentoxy, hexoxy, heptoxy, octoxy, methoxymethyl, ethoxymethyl, propoxymethyl, butoxymethyl, methoxyethyl, ethoxyethyl or propoxyethyl. Formula Ig4-
Compounds in which the terminal groups of 1, Ig4-3, Ig4-4 and Ig4-10 are symmetrically substituted are particularly preferred. Compounds of formulas Ig4-1 to Ig4-10 can have one of the 1,4-phenylene groups laterally mono-substituted by F or Cl. In this case, it is preferable to substitute 2 or 3 sites with F. Further preferred are compounds of the formula Ig4-9.

Compounds of the formula Ig are described, for example, in DE 2,167,25
2, DE2,800,553, DE2,536,046, DE2,
Prepared by transesterification of appropriately substituted phenols or phenoxides with appropriately substituted carboxylic acids or reactive carboxylic acid derivatives as described in 123,175 and DE 2,139,628. preferable.

Formula Ig, especially Ig2-1, Ig2-2, Ig2-1a-1d, Ig
Liquid crystal mixtures containing one or more compounds selected from the group consisting of 2-2a to 2c, Ig3-1 to Ig3-10 and Ig4-1 to Ig4-10 are advantageous values for Δε, high stability, easy It is characterized by good manufacturability, low miscibility with the polymers used for the matrix, and especially favorable values for the wide mesogenic range, relatively high clearing points and birefringence and flow viscosity.

These liquid crystal mixtures have a content of 1 to 40%, especially 5%.
It preferably contains 30% of a compound of the formula Ig, particularly the preferred subformulae. In this case, the liquid-crystal mixture preferably contains compounds of the formula Ig, particularly preferably 1 to 5, especially 1 to 3, of the lower formulas.

Formula Ig, particularly preferred Formulas Ig2-1 to Ig2-2, Ig2-
1a-1d, Ig2-2a-2c, Ig3-1-Ig3-10 and Ig4-1-Ig4
Particularly preferred is a liquid crystal mixture containing one or more compounds selected from the compound group of -10 and one or more compounds selected from the group of compounds II1 to II28, III1 to III3, and IV1 to IV8.

In the liquid-crystal mixtures used according to the invention, at least one compound of the formula Ig, particularly a preferred sub-formula, and furthermore the formulas II1-II28, III1- and III3 and IV1-IV8
Is preferably from 15% to 100%, especially from 25% to 100%.

Liquid crystal mixtures based on component mixtures consisting of at least one laterally unsubstituted compound of the formula Ig2-1 and one or more compounds of the formula IV1 are highly preferred for matrix systems, but on the contrary This is not very desirable for network structures. However, besides the compounds of these formulas, formulas Ia, Ic, Id, Ie, IfF, IfCl, IfCl.F, Ih
Alternatively, liquid-crystal mixtures containing Ii, at least one compound selected from the group of particularly preferred sub-formulas, are generally also preferred for the network system.

Particular preference is also given to the following small group of component mixtures T (Ig), each containing at least one compound from the substance groups indicated in each case.

[0326]

[Table 27]

Preference is given to liquid-crystal mixtures based on the following component mixtures T (Ig) 4 to 6, each containing at least one compound from the compounds of the formulas mentioned in each case. The following table further shows the preferred masses of these compounds in the component mixture. The component mixture contains 2 to 38, preferably 2 to 35, especially 2 to 25 compounds. The sum of the masses of these compounds in the component mixture is 10
0%. The mass of the component mixture in the liquid crystal of the present invention is 10
% To 100%, especially between 15% and 100%, more particularly between 25% and 100%.

[0328]

[Table 28]

Formula Ih R ¹ -Q ⁶ -C≡CQ ⁷ -R ² Ih (wherein at least one of the two radicals R ¹ and R ² is
Wherein ^one of the two groups R ¹ and R ² is
Also known as F, Cl, OCF ₃ , OCHF ₂ or CF ₃ , Q ⁶ and Q
⁷ in each case independently of each other,

[0330]

Embedded image And Q ⁶ is

[0331]

Embedded image And Q ⁷ is

[0332]

Embedded image Are also preferred liquid crystal mixtures.

The compounds of formula Ih are preferably of the following formulas I2h-1 to I2h-3
And bicyclic compounds which are preferred.

R ¹ -Phe-C≡C-Phe-R ² Ih2-1 R ¹ -Pyr-C≡C-Phe-R ² Ih2-2 R ¹ -Pyd-C≡C-Phe-R ² Ih2- Three

In the compounds of the formulas Ih2-1 to Ih2-3 having two nonpolar groups, R ¹ and R ² are independently from each other 1 to 1
Preference is given to alkyl or alkoxy having 0, especially 1 to 8, C atoms, furthermore also n-alkoxyalkyl, especially n-alkoxymethyl and n-alkoxyethyl. One of the 1,4-phenylene groups contained in the compounds of the formulas Ih2-1 to Ih2-3 can be substituted at two or three positions by Cl or F, in particular by F.

R ¹ -Phe-C≡C-Phe-R ² Ih2-1d R ¹ -Phe.3F-C≡C-Phe-R ² Ih2-1e R ¹ -Phe.2F-C≡C-Phe- R ² Ih2-1f R ¹ -Phe-C≡C-Phe.2F-R ² Ih2-1g R ¹ -Phe-C≡C-Phe.3F-R ² Ih2-1h R ¹ -Phe-C≡C- Pyr-R ² Ih2-2b R ¹ -Phe-C≡C-Pyd-R ² Ih2-3b R ¹ -Pyr-C≡C-Phe-R ² Ih2-2c R ¹ -Pyd-C≡C-Phe- R ² Ih2-3c (where R ¹ is F, Cl, OCF ₃ , OCHF ₂ , or CF ₃ ;
And R ² are alkyl or alkoxy having 1 to 7 C atoms)

[0337] compounds of the formula I h, the following sub-formula Ih3-1~Ih3
And a tricyclic compound which is preferably a compound of the formula:

R ¹ -Phe-C≡C-Phe-Phe-R ² Ih3-1 R ¹ -Phe. (F) -C≡C-Phe-Cyc-R ² Ih3-2 R ¹ -Pyr-C≡ C-Phe-Phe-R ² Ih3-3 R ¹ -Pyd-C≡C-Phe-Phe-R ² Ih3-4 R ¹ -Pyr-C≡C-Phe-Cyc-R ² Ih3-5 R ^1- Pyd-C≡C-Phe-Cyc-R ² Ih3-6 R ¹ -Cyc-CH ₂ CH ₂ -Phe-C≡C-Phe-R ² Ih3-7 R ¹ -Cyc-CH ₂ CH ₂ -Phe- C≡C-Pyd-R ² Ih3-8 R ¹ -Cyc-CH ₂ CH ₂ -Phe-C≡C-Pyr-R ² Ih3-9 R ¹ -Cyc-COO-Phe-C≡C-Phe. in the compounds of F) -R ² Ih3-10 subformula Ih3-1~Ih23-10, R ¹ and R ² of compounds having two nonpolar, independently of one another 1 to 1
Those which are n-alkyl or n-alkoxy having 0 C atoms are preferred, and also n-alkoxymethyl or n-alkoxyethyl having 1 to 8 C atoms. Formula Ih3 having a polar group F, Cl, OCHF ₂ , OCF ₃ or CF ₃
Compounds of -1 to Ih3-10 (where the other group is an alkyl group or alkoxy having 1 to 8 C atoms) are preferred. The compounds of the formulas Ih3-1 to Ih3-10 have in each case one of the 1,4-phenylene groups present in the molecule X = F or Cl
Can be laterally mono-substituted. The following monosubstituted formulas Ih3-1a-1d, Ih3-2a-2b, Ih3-5a and Ih3-6a
6b are particularly preferred.

R ¹ -Phe-C≡C-Phe-Phe.3F-R ² Ih3-1a R ¹ -Phe-C≡C-PhePhe.3Cl-R ² Ih3-1b R ¹ -Phe-C≡C- Phe.3F-Phe-R ² Ih3-1c R ¹ -Phe-C≡C-Phe.3Cl-Phe-R ² Ih3-1d R ¹ -Phe-C≡C-Phe.3F-Cyc-R ² Ih3- 2a R ¹ -Phe-C≡C-Phe.3Cl-Cyc-R ² Ih3-2b R ¹ -Pyr-C≡C-Phe-Phe.FR ² Ih3-5a R ¹ -Pyd-C≡C-Phe- Phe.FR ² Ih3-6a R ¹ -Pyd-C≡C-Phe.F-Phe-R ² Ih3-6b (However, in the compounds of the formulas Ih3-1a to 1d, Ih3-5a and Ih3-6a to 6b, in particular the compounds of R ² and formula Ih3-2a～2b, especially compounds of the a) formula Ih R ¹ is a polar group is preferably a the following compounds of sub-formulas Ih4-1～Ih4-5 4
Including cyclic compounds.

R ¹ -Phe-Phe-C≡C-Phe. (F) -Phe. (F) -R ² Ih4-1 R ¹ -Phe-Phe. (F) -C≡C-Phe-Cyc- R ² Ih4-2 R ¹ -Cyc-Phe-C≡C-Phe. (F) -Cyc-R ² Ih4-3 R ¹ -Cyc-CH ₂ CH ₂ -Phe-C≡C-Phe. (F) -Cyc-R ² Ih4-4 R ¹ -CyC-CH ₂ CH ₂ -Phe-C≡C-Phe. (F) -Cyc-R ² Ih4-5

[0341] In the compounds of formula Ih4-1～Ih4-5, it is preferably one of the radicals R ¹ and R ² Ru Ah with a polar group, and the other is methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, Octyl, nonyl, decyl, methoxy,
Preference is given to ethoxy, propoxy, butoxy, pentoxy, hexoxy, heptoxy, octoxy, methoxymethyl, ethoxymethyl or propoxymethyl. Symmetrically substituted compounds of the formulas Ih4-1 and Ih4-3 having two non-polar groups are more preferred. Formulas Ih4-1 to Ih4
Compound -5 can have one of the 1,4-phenylene groups laterally mono-substituted by F or Cl. In this case, substitution at three sites is preferred.

The compound of formula Ih is DE 2,226,376, GB
2,155,465, GB2,189,785, DE3,711,
306, JP61-260,031, DE3,710,069,
JP02-062,861, JP63-060,972, EP0,
It is preferably prepared by the methods described in 255,700 and EP 0,276,067.

Compound Ih, particularly preferred compounds Ih2-1 to Ih2
-3, Ih2-1a-1h, Ih2-2a-2c, Ih2-3a-3c, Ih3-1-Ih3
-10, Ih3-1a to 1d, Ih3-2a to 2b, Ih3-5a, Ih3-6a to 6b and a liquid crystal mixture containing one or more compounds selected from the group of compounds Ih4-1 to Ih4-5 are: Wide mesogenic range,
It is characterized by a relatively high clearing point, a high stability, a low miscibility with the polymer used for the matrix, and advantageous values and birefringence, especially with regard to dielectric anisotropy and viscosity.

These liquid crystal mixtures have a content of 1 to 40%, especially 5%.
It preferably contains 30% of a compound of the formula Ih, particularly the preferred subformulae. In this case, the liquid-crystal mixture preferably contains the compounds of the formula Ih, in particular of the preferred subformulas 1 to 5, in particular 1 to 3.

At least one compound selected from the group of compounds of the formula Ih, particularly preferred lower formulas, and further compounds
Liquid crystal mixtures containing one or more compounds selected from the group of II1-II28, III1-III3 and IV1-IV8 are particularly preferred.

In the liquid-crystal mixtures used according to the invention, at least one compound of the formula Ih, particularly preferred sub-formulas, and additionally the compounds of the formulas II1-II28, III1- and III3 and IV1-IV8
Is preferably from 15% to 100%, especially from 25% to 100%.

Liquid-crystal mixtures based on component mixtures consisting of at least one compound of the formula Ih2-1 and also at least one compound of the formulas IV1 and / or IV2 are generally particularly preferably applied to matrix systems. However, they are often not very suitable for application to network structures. The same applies to liquid crystals based on component mixtures containing at least one compound of the formulas Ih3-10 and / or Ih3-2 and at least one compound of the formula IV4. However, the properties of such mixtures are compounds Ia, Ic, Id, I
e, IfF, IfCl, IfCl.F, Ig and II1 to II28, which can be improved by adding at least one compound selected from the group of particularly preferred subformulae compounds, so that their mixtures also have a network structure Found that it can be applied to

The liquid-crystal mixtures based on the component mixtures T (Ih) of the following subgroups, each containing at least one compound from the group of compounds of the formulas indicated in each case, can be used in both matrix and network systems: Preferred. The table below shows the preferred masses of these compounds in the component mixture.
[%] Is further indicated.

[0349]

[Table 29]

The following small group of component mixtures, each containing at least one compound from the group of compounds indicated in each case, are preferred for application to the matrix system:
It is particularly preferable for a network structure system.

[0351]

[Table 30]

Formula Ii R ¹ -Q ⁸ -CH ₂ CH ₂ -Q ⁹ -R ² Ii wherein R ¹ and R ² are each independently of the meanings indicated in R ^{1 of} claim 1 And Q ⁸ and Q ⁹ independently of one another in each case trans-1,4-cyclohexylene, 1,4-phenylene, 4,4′-biphenylyl, 4,4′-cyclohexylphenyl, 4, 4'-phenylcyclohexyl or trans-, trans-4
A liquid crystal mixture comprising at least one compound of the formula: 4'-bicyclohexyl (wherein one of the 1,4-phenylene groups present in the molecule may be replaced by fluorine or chlorine). Is more preferred.

Compounds of formula Ii are preferably of the following formulas Ii2-1 and I
i2-2 bicyclic compounds. R ¹ -Phe-CH ₂ CH ₂ -Phe-R ² Ii2-1 R ¹ -Cyc-CH ₂ CH ₂ -Phe-R ² Ii2-2

Preferably, R ¹ and R ^{2 in} the compounds of the formula Ii2 independently of one another are alkyl or alkoxy having 1 to 10, in particular 1 to 8, C atoms. More preferred are n-alkoxyalkyl compounds, especially n-alkoxymethyl and n-alkoxyethyl compounds. Two 1,4-
One of the phenylene groups can be substituted at two or three positions by Cl or F, especially by F at three positions.

The compound of the following formula is particularly preferred. Alkyl or alkoxy-Phe-CH ₂ CH ₂ -Phe-R ² Ii2-1a Alkyl or alkoxy-Phe.3F-CH ₂ CH ₂ -Phe-R ² Ii2-1b Alkoxymethyl-Phe.2F-CH ₂ CH ₂ -Phe-R ² Ii2-1c Alkyl or alkoxy-Cyc-CH ₂ CH ₂ -Phe-R ² Ii2-2a

The compounds of formula Ii have the following sub-formulae Ii3-1 to Ii3:
-5 include tricyclic compounds of subformula Ii3, which are preferably compounds of formula Ii3. R ¹ -Phe-CH ₂ CH ₂ -Phe-Phe -R ² Ii3-1 R ¹ -Cyc-CH ₂ CH ₂ -Phe-Phe -R ² Ii3-2 R ¹ -Phe-CH ₂ CH ₂ -Phe- ^{Cyc- R 2 Ii3-3 R 1 -Phe-} Cyc-CH 2 CH 2 -Phe- R 2 Ii3-4 R 1 -Cyc-CH 2 CH 2 - Phe-Cyc- R 2 Ii3-5 R 1 -Cyc- _{cyc-CH 2 CH 2 -Phe- R} 2 Ii3-6

In the compounds of the formulas Ii3-1 to Ii3-6, R ¹ and R ² independently of one another have n to 1 to 10 C atoms
-Alkyl or n-alkoxy, and also n-alkoxymethyl or n-alkoxyethyl having 1 to 8 C atoms. The compounds of formulas Ii3-1 to Ii3-6 can be laterally monosubstituted with one of the 1,4-phenylene groups, X = F or Cl. Lateral unsubstituted compounds of formulas Ii3-1 to Ii3-6 and formulas Ii3-1a to Ib wherein Phe.X is a 1,4-phenylene group laterally monosubstituted by F or Cl at two or three sites , Ii3-2a, I
Particularly preferred are laterally mono-substituted compounds of i3-3a, Ii3-6a and Ii3-5a.

R ¹ -Phe-CH ₂ CH ₂ -Phe-Phe.3X-R ² Ii3-1a R ¹ -Phe-CH ₂ CH ₂ -Phe.X-Phe-R ² Ii3-1b R ¹ -Cyc- CH ₂ CH ₂ -Phe-Phe.2X-R ² Ii3-2a R ¹ -Phe-CH ₂ CH ₂ -Phe.X-Cyc-R ² Ii3-3a R ¹ -Cyc-CH ₂ CH ₂ -Phe.2F -Cyc-R ² Ii3-5a R ¹ -Cyc-Cyc-CH ₂ CH ₂ -Phe.FR ² Ii3-6a Laterally monosubstituted compounds of formulas Ii3-1 to Ii3-6 are generally the corresponding unsubstituted compounds Characterized by lower flow viscosity.

Q ⁸ and Q ⁹ are each independently of the other

[0360]

Embedded image It further includes certain tetracyclic compounds.

R ¹ -Phe-Phe -CH ₂ CH ₂ -Phe. (F) -Phe-R ² Ii4-1 R ¹ -Phe-Phe -CH ₂ CH ₂ -Phe. (F) -Cyc-R ² Ii4-2 R ¹ -Phe-Cyc -CH ₂ CH ₂ -Phe. (F) -Phe. (F) -R ² Ii4-3 R ¹ -Phe-Cyc -CH ₂ CH ₂ -Phe. (F)- Cyc-R ² Ii4-4 R ¹ -Cyc-Phe. (F) -CH ₂ CH ₂ -Phe-Cyc-R ² Ii4-5 R ¹ -Cyc-Cyc -CH ₂ CH ₂ -Phe. (F)- Phe-R ² Ii4-6

The radicals R ¹ and R ^{2 in} the compounds of the formulas Ii4-1 to Ii4-6 are, independently of one another, methyl, ethyl, propyl,
Butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, heptoxy, octoxy, methoxymethyl, ethoxymethyl, propoxymethyl, butoxymethyl, methoxyethyl, methoxyethyl, ethoxyethyl or propoxyethyl It is preferred that Formula Ii4-1
The compounds of ~ Ih4-6 can be laterally monosubstituted with one of the 1,4-phenylene groups by F or Cl. In this case, substitution at three sites is preferred. These monosubstituted tetracyclic compounds are characterized by a high clearing point and a relatively low flow viscosity η.

Compounds of formula Ii are described in EP-0,084,194, JP
61-087,777, GB2,201,415 and DE3,
237,367.

Formula Ii, particularly preferred Formulas Ii2-1, Ii2-2, Ii2-
1a-1c, Ii2-2a, Ii3-1-Ii3-5, Ii3-1a-1b, Ii3-2a,
A liquid crystal mixture containing one or more compounds selected from the group consisting of Ii3-6a, Ii3-3a, Ii3-5a and Ii4-1 to Ii4-5 has high stability and low miscibility with the polymer used for the matrix. It is characterized by advantageous properties with regard to the properties and especially the wide mesogenic range, the relatively high clearing point and the optical anisotropy Δn and the flow viscosity η.

These liquid crystal mixtures have a content of 1 to 40%, especially 5%.
It preferably contains 30% of the compounds of the formula Ii, particularly the preferred subformulae. In this case, the liquid-crystal mixture preferably contains 1 to 5, especially 1 to 3, compounds of the formula Ii, particularly preferred lower formulas.

At least one compound selected from the group of compounds of the formula Ii, particularly preferred subformulas, and further compounds of the formulas II1-II2
Liquid crystal mixtures containing one or more compounds selected from the group consisting of 8, III1-III3 and IV1-IV8 are particularly preferred.

In the liquid-crystal mixtures used according to the invention, at least one compound of the formula Ii, particularly preferred sub-formulas, and additionally the compounds of the formulas II1-II28, III1- and III3 and IV1-IV8
Is preferably from 15% to 100%, especially from 25% to 100%. These component mixtures are preferred for network systems and matrix systems.

The liquid-crystal mixtures according to the invention have the formula I, in particular the formulas Ia to Ia
It contains one or more compounds selected from the compound group of i. In this case, preference is generally given to liquid-crystal mixtures which, in addition to one or more compounds of the formula I, in particular of the formulas Ia to Ii, additionally comprise one or more compounds selected from the group of the compounds II to IV.

More preferred are liquid crystal mixtures containing at least one compound from each of two different compounds selected from the compounds of formulas Ia-Ii.

Particular preference is given to the component mixtures T (Ii) of the following subgroups each containing at least one compound from the class of compounds of the formulas indicated in each case:

[0371]

[Table 31]

Preference is given to liquid-crystal mixtures based on the following component mixtures T (Ii) 9 to 13, each containing at least one compound from the compounds of the formulas mentioned in each case. The following table further shows the preferred masses of these compounds in the component mixture. The component mixture contains 2 to 38, preferably 2 to 35, especially 2 to 25 compounds. The sum of the masses of these compounds in the component mixture is 10
0%. The mass of the component mixture in the liquid crystal of the present invention is 10
% To 100%, especially between 15% and 100%, more particularly between 25% and 100%.

[0373]

[Table 32]

The component mixtures T (I) shown below contain at least one compound from the group of compounds given in each case, and liquid-crystal mixtures containing one or more of these component mixtures are particularly very suitable. Preferred.

[0375]

[Table 33]

Those skilled in the art will recognize that this preferred mixture of components is such that the liquid crystal mixture is optimized for a particular application.
It can be immediately selected from the group of T (I) 1 to T (I) 22. For example, T (I) 1 has a particularly high dielectric anisotropy, whereas component mixtures T (I) 16 to T (I) 18 have particularly high stability, and component mixtures T (I) 4, T (I) 11 and T
(I) 19 is characterized by a relatively high clearing point. Choosing the appropriate component mixture is not difficult for one skilled in the art and does not require any inventive assistance.

Each of at least one compound from two compound groups selected from compound groups Ia to Ii and
Liquid crystal mixtures containing at least one compound selected from the group consisting of II1-II28, III1-III3 and IV1-IV8 are more particularly preferred. In this case, one of the preferred component mixtures T (I) to T (I) 22 and formulas II1, II2, II3,
II4, II5, II6, II7, II8, II9, II10, II12, II13, I
I16, II17, II18, II19, II20, II21, II25, II27, II2
Liquid crystal mixtures containing compounds selected from the compounds of 8, III1, III2, IV1, IV2, IV3, IV4, IV5 and IV6 are particularly highly preferred.

In addition to one or more compounds selected from the group of compounds Ia, Ib, Ic, Id, Ie, If, Ig and Ii and at least one compound selected from the group of compounds of the formulas II to IV, Ih *

[0379]

Embedded image Wherein R ³ is an alkyl group having 1 to 10 C atoms which can also replace the CH ₂ group with —O— or —CH = CH—, and Z ¹³ is a single bond, —COO— or — CH ₂ CH ₂ —,
X ⁷ and X ⁸ are independently CH or N, L ¹ and L ² are independently H or F, e is 0 or 1, and Y ³ is F, Cl, CF ₃ , OCF ₃ or O
CHF ₂ ). Still more preferably, a liquid crystal mixture containing another compound.

The compounds of the formula Ih * have a polar group F, Cl, CF ₃ , OCF ₃ or OCHF ₂ and fall into some of the compounds of the formula Ih. The compounds specified below are more preferred compounds.

R ³ -Phe-C≡C-Phe.3F5F-Y ³ Ih * 2-1 R ³ -Pyd-C≡C-Phe.3F5F-Y ³ Ih * 2-2 R ³ -Pyr-C≡ C-Phe.3F5F-Y ³ Ih * 2-3 R ³ -Cyr-Pyr-C≡C-Phe.3F5F-Y ³ Ih * 3-1 R ³ -Cyc-Pyd-C≡C-Phe. (F , 2) -Y ³ Ih * 3-2 R ³ -Cyc-CH2CH2-Pyr-C≡C-Phe. (F, 2) -Y ³ Ih * 3-3 R ³ -Cyc-COO-Pyd-C≡ C-Phe. (F, 2) -Y ³ Ih * 3-4

Preferred liquid-crystal mixtures which contain, in addition to at least one compound of the formulas Ia to Ig and at least one compound of the formulas II to IV, at least one compound of the formula Ih * as a third essential component, are now described. One of the preferred compounds and / or formulas Ih2-1 to Ih2-2, Ih2-1a to 1h, Ih2-2a to 2c,
Ih2-3a ~ 3c, Ih3-1 ~ Ih3-10, Ih3-1a ~ 1d, Ih3-2a ~ 2
b, preferably one of the preferred compounds Ih3-5a, Ih3-6a-6b and Ih4-1-Ih4-5.

These mixtures are distinguished by high stability and high birefringence, and are particularly suitable for application in matrix systems and are very particularly suitable for network systems.

In this case, the mass of the compounds selected from the group of compounds of the formulas Ih and Ih * is greater than 5%, in particular 7.5%
As mentioned above, it is particularly preferred that it is more than 10%, and more particularly it is more than 20%. The third essential component of these liquid crystal mixtures is

[0385]

Embedded image Very particular preference is given to the compounds of the formula wherein L ¹ , Y ³ and e are as defined above.

At least one compound of the formula II,
Particular preference is also given to mixtures based on a component mixture containing at least one compound of the formula IV8 and at least one compound of the formula Ih *. In this case, the following subgroups of component mixtures, each containing at least one compound from each of the groups E, F, and G, are particularly preferred. In this case, the weight of the compounds from each group in the component mixture is preferably in the indicated weight percentage range.

[0387]

[Table 34]

The sum of the masses of the compounds from groups E, F and G in the component mixture is 100%, and the mass of the component mixture in the liquid crystal mixture which can be used according to the invention is 25-100%. Is preferred.

Compounds Ia, Ib, Ic, Ie, Ig, Ih and Ii
In addition to one or more compounds selected from and at least one compound selected from the group of compounds of formulas II-IV,

[0390]

Embedded image (Wherein ring A ¹⁵ is trans-1,4-cyclohexylene or 1,4-phenylene, and R ³ , Z ¹³ , X ⁷ , X ⁸ ,
L ¹ , e and Y ³ are as defined above). Still more preferably, a liquid crystal mixture containing another compound. Compounds of formula If * have the formulas IfF, IfCl and I
It refers to a preferred small group of compounds selected from the compounds of fCl.F. The mass of the compounds of the formula If * in at least three-component liquid-crystal mixtures of this kind can be greater than 5%, in particular greater than 10%, more than 20% and particularly preferably up to 55%. Liquid crystal mixtures of this kind have advantageous properties and are distinguished by particularly high stability and advantageous values of the optical parameters. Liquid crystal mixtures containing at least one compound of the formulas Ia to Ie and Ig to Ii and at least one of the following preferred compounds in addition to the compounds of the formulas II to IV are very particularly preferred.

[0391] ^{R 3 -Phe-Phe. (F} ) -FR 3 -Phe-Phe. (F) -Cl R 3 -Pyd-Phe-F R 3 -Pyd-Phe.3F-FR 3 -Pyd-Phe- Cl R ³ -Pyd-Phe.3F-Cl R ³ -Pyr-Phe-F R ³ -Pyr-Phe.3F-FR ³ -Pyr-Phe-Cl R ³ -Pyr-Phe.3F-Cl

The first essential component comprises at least one compound of the formulas Ia to Ie whose mass in the component mixture is 10% to 90%; the second essential component is the compound II1, II2, I
I3, II4, II5, II6, II7, II8, II9, II16, II17, II18,
II25, II26, II27, II28, III1, III2, IV1, IV2, IV3,
Comprising one or more compounds selected from the group of IV4, VI7 and IV8, wherein the mass of this component in the component mixture is from 5 to 80%
And the third essential component is the above-mentioned preferred 2
1 or more and / or the following compound R ³ -Cyc-Phe-Phe cyclic ^{compound. (F) -FR 3 -Cyc-} Phe-Phe. (F) -Cl R 3 -Phe-Pyr-Phe. ( (F) -FR ³ -Phe-Pyr-Phe. (F) -Cl R ³ -Phe-Pyr-Phe. (F) -CF ₃ R ³ -Phe-Pyd-Phe. (F) -FR ³ -Phe- Pyr-Phe. (F) -Cl R 3 -Phe-Pyr-Phe. (F) -OCF include one or more _3, the weight of component a mixture of 5% to 6
5%, especially 10% to 65%, more particularly 12.5%
Particularly preferred are component mixtures that are ~ 65%.

The total weight of the component mixtures is 100%, and the weight of the component mixture in the optimum mixture is 25 to 10%.
It is preferably 0%.

In addition to one or more compounds selected from the group of compounds of formulas Ia-Ie and Ig-Ii and one or more compounds selected from the group of compounds of formulas II-IV,

[0395]

Embedded image (Wherein ring A ¹⁶ is trans-1,4-cyclohexylene, 1,1
A liquid-crystal mixture further comprising at least one compound of 4-phenylene or 3-fluoro-1,4-phenylene and at least one of Z ¹³ , L ¹ , Y ³ , R ³ and e having the meaning given above, Particularly preferred. Compounds of formula If ** have the formulas IfF, IfC
and a preferred small group of compounds selected from compounds of l and IfCl.F.

In addition to the compounds of the formulas Ia to Ie and Ig to Ii,
Liquid-crystal mixtures containing compounds of the formulas I to IV and further of the compound of the formula If ** are characterized by favorable properties, in particular high stability, an advantageous operating temperature range and an advantageous threshold voltage. Preferably, the mass of the compound of the formula If ** in these liquid-crystal mixtures is more than 5%, in particular more than 10%, more particularly more than 15%. The following small group of compounds of the formula If ** are very particularly preferred.

[0397] ^{R 3 -Cyc-COO-Phe.} (F) -Y 3 If ** 2-1 R 3 -Phe-COO-Phe. (F) -Y 3 If ** 2-2 R 3 -Cyc- (F) -Y ³ If ** 3-1 R ³ -Cyc-Phe-COO-Phe. (F) -Y ³ If ** 3-2 The following liquid-crystal mixtures, each containing at least one compound from the groups I and K respectively in the indicated mass range, are very particularly preferred.

[0398]

[Table 35]

In this case, the total mass in the component mixture is 1
It is preferably 00% and the weight of the component mixture in the liquid crystal mixture used according to the invention is from 10 to 85%.

The liquid crystals according to the invention can be prepared, in addition to the compounds of the formula I according to the invention, in particular of the preferred sub-formulas, more particularly of the preferred liquid-crystal mixtures, in addition to nematic or nematic-forming (mono- or isotropic) substances, in particular azoxybenzene , Benzylideneanilines, biphenyls, terphenyls, phenyl or cyclohexyl benzoates, phenyl or cyclohexyl esters of cyclohexanecarboxylic acid, phenyl or cyclohexyl esters of cyclohexylbenzoic acid, phenyl or cyclohexyl esters of cyclohexylcyclohexanecarboxylic acid Benzoic acid, cyclohexanecarboxylic acid or cyclohexylcyclohexanecarboxylic acid cyclohexylphenyl esters, phenylcyclohexanes, cyclohexylbiphenyls, Phenylcyclohexylcyclohexanes, cyclohexylcyclohexanes, cyclohexylcyclohexylcyclohexenes, 1,4-bis
-Cyclohexylbenzenes, 4,4'-bis-cyclohexylbiphenyls, phenyl or cyclohexylpyrimidines, phenyl or cyclohexylpyridines,
Phenyl or cyclohexyldioxane, phenyl
-Or cyclohexyl-1,3-dithiane, 1,2-diphenylethane, 1,2-dicyclohexylethane, 1
-Phenyl-2-cyclohexylethanes, 1-cyclohexyl-2- (4-phenylcyclohexyl) ethanes, 1-
Cyclohexyl-2-biphenylethanes, 1-phenyl-
It is preferably selected from the group consisting of 2-cyclohexylphenylethanes, optionally halogenated stilbenes, benzylphenyl ethers, tolanes and substituted cinnamic acids. Further components may be included. The 1,4-phenylene groups of these compounds can also be fluorinated.

In these compounds, both terminal groups are preferably in each case independently of one another alkyl, alkenyl, alkoxy, alkenyloxy or alkanoyloxy having up to 8 C atoms. In most of these compounds, both terminal groups are different from one another, one of which is usually alkyl or alkenyl.

However, if one and / or both terminal groups are polar groups —CN, —NCS, —F, —Cl or (O) _i CX _k H
_{It can also be 3-k} , where i is 0 or 1, k is 1, 2 or 3, and X is F or Cl. If only one of the terminal groups is one of the polar groups mentioned above, the other is preferably alkyl or alkenyl.

Many substances of this type, or alternatively mixtures thereof, are commercially available. All these substances are obtained by methods known according to the literature or according to them.

The liquid crystals used in the electro-optical liquid crystal system according to the invention preferably contain from 1% to 10%, in particular from 10% to 100%, more particularly from 20% to 100%, of the compound of the formula I. . In this case, 1 to 20, especially 1 to 15, formulas
Liquid crystal mixtures containing the compounds of I are preferred. If the liquid-crystal compounds of the formula I are selected from only one subgroup of the formulas Ia to Ii, the liquid-crystal mixture preferably contains 1 to 5, in particular 1 to 3, compounds of this sub-formula of the formula I.

The liquid crystal mixtures according to the invention have the formulas I, II, III and
Preferably, it is based on a compound selected from the group IV. The mass of compounds selected from the group of the formulas I, II, III and IV in the liquid-crystal mixture is from 5% to 100%, in particular from 10% to 1%.
It is preferably 00%, more particularly 15% to 98%. The liquid crystal mixtures according to the invention have the formulas I, II, III, VI and V
It is preferable to contain 2 to 40 compounds, particularly 2 to 38 compounds, more particularly 2 to 35 compounds selected from the group of

The dielectric anisotropy of the liquid crystal mixture used is positive,
That is, Δε> 0, preferably Δε> 3.

When the value of the dielectric anisotropy Δε is small, a very high threshold voltage is observed. Particularly preferred values are Δε>
5 and Δε> 8 are very particularly preferred.

Liquid crystal mixtures based on compounds having a medium polarity of 3 ≦ Δε ≦ 20 (* 1), especially 3 ≦ Δε ≦ 15 (* 2), have particularly advantageous properties,
In particular, they have been found to have high temperature and UV stability and high specific resistance. Mixtures of this kind are also particularly suitable for systems with a high information content controlled by means of active or passive matrices, and more particularly for systems which have to withstand relatively high operating temperatures (for example systems for use in the field). ing. Preferably, the mass of the moderately polar compound in the liquid crystal mixture is at least 50%, in particular at least 60%, more particularly at least 65%.

Particularly, W = -F, -Cl, -CF ₃ , -OCF ₃ , -OCHF
₂ or NCS, especially W is -F, -Cl, -CF ₃ , -OCF ₃ or -OCHF
Compounds of the formula I which are ₂ are preferred ranges (* 1) or (*
Liquid crystal compounds often having a dielectric constant in 2), while W = -CN, often have excessively high dielectric constants, which proved to be less suitable for such mixtures. The mass of the compound having terminal carbonitrile groups in the liquid-crystal mixture based on compounds of moderate polarity is preferably less than 15%, in particular 10% or less. For example, if a highly polar additive with Δε> 20 is required to lower the threshold voltage, one end group has the meaning indicated for R ¹ and the other end group has

[0410]

Embedded image (However, W is -F, -Cl, -CF ₃ , -OCF ₃ or -OCHF ₂
And Y is H or F).

Compounds in which W = -Cl are generally characterized by a higher birefringence Δn than the corresponding compounds in which W = -F, and thus, for example, when high birefringence is desired to enhance scattering in opaque conditions Often preferred.

The present invention provides the person skilled in the art with a limited group of particularly preferred compounds of the formula I, in particular of the formulas Ia to Ii, and particularly preferred liquid-crystal component mixtures. Formula I, in particular one of the formulas Ia to Ii
A liquid-crystal mixture containing at least one compound, more particularly at least one of the abovementioned component mixtures, corresponds to the requirements mentioned at the outset set for use in an electro-optical system according to the preamble of claim 1, It has particularly high advantageous properties, to a high degree, and much better than the liquid-crystal mixtures conventionally named for these systems. In this case, based on the detailed description, those skilled in the art will recognize that birefringence Δn and / or ordinary refractive index n ₀ and / or other refractive indices and / or viscosity and / or dielectric anisotropy and / or Or further parameters of the clearing point and / or liquid crystal and / or threshold voltage and / or further parameters of the system and / or their temperature dependence and / or operating temperature range and / or monomers or oligomers for polymerization And / or from the preferred liquid crystal compounds and liquid crystal mixtures of the group described without inventive assistance to optimize the solubility of the liquid crystal in the coarse matrix or the coarse network and / or the further parameters of the liquid crystal and the system. But you can choose.

If, for example, a high clearing point is required, the person skilled in the art will recognize that the mass of the bicyclic compound in the liquid-crystal mixture is not too high and that the compounds of the formula I, in particular of the sub-formulas Ia to Ii, and the preferred component mixture It is preferable to select from among them. In addition, one skilled in the art will appreciate that, for example, tetracyclic compounds of formulas Ie4-1 to Ie4-4, or also, for example, R ⁴ -Phe-Phe-Cyc-R ⁵ R ⁴ -Cyc-Phe-Phe-Chec-R ⁵ Other high transparent point imparting substances can be added to the liquid crystal.

In these compounds, R ⁴ and R ⁵ are
Preference is in each case, independently of one another, of alkyl, methoxy, alkoxycarbonyl or alkanoyloxy having 1 to 15 C atoms.

Additives of this kind are known to the person skilled in the art and can be selected without problems from the above-listed substances. In this case, the person skilled in the art is particularly aware of Δn and / or n ₀ and / or
Or other refractive indices and / or Δε to be adjusted in certain embodiments of the electro-optic system of the present invention and / or Δε and / or further physical parameters that are important to the particular application are acceptable and / or slightly less. It is preferred to choose the concentration of such additives such that they have only a negligible effect.

When the system of the present invention is controlled using, for example, an AC voltage, it is necessary to use a highly viscous liquid crystal mixture. Otherwise, a flickering display will result, especially at low or medium frequencies. To increase the viscosity, those skilled in the art can add highly viscous liquid crystal compounds to the liquid crystal mixture. Preferably, these compounds are selected from the group of compounds of the formula I, in particular of the formulas Ia to Ii, but they can also be employed from the abovementioned substance groups. In particular, DE 3,919,9
As described at 42, polymers having one or more side groups can be added to increase the viscosity. On the other hand, when the electro-optical system is used, for example, as a matrix display with a high information content, a high-viscosity liquid crystal mixture is used.
Particularly suitable for achieving short switching times.

In this case, the person skilled in the art must be aware of the formula I, in particular the sub-formula Ia, so that the content of tri- and tetracyclic compounds is not too high.
It is preferable to select from the group of compounds of ~ Ii. If it is necessary to use a high content of tri- and tetracyclic compounds to achieve a high clearing point, one skilled in the art generally chooses laterally fluorinated or chlorinated compounds of formulas Ia-Ii. However, those skilled in the art, for example, selected from ^{R 4 -Cyc-Phe.3F-Phe-} R substance groups listed above having a low viscosity, such as ^5, it may be added them to the liquid crystal mixtures according to the invention it can. R ⁴ and R ^{5 in the} compounds given by way of example are preferably as defined above.

[0418] Those skilled in the art, for example Δε and acceptable to the critical parameters of the liquid crystal mixture as particular T _c when using the viscosity-reducing agent and / or minor and /
Alternatively, the substances used to improve the viscosity and their concentration are selected so as to have a negligible effect.

If desired, one skilled in the art can take into account that other parameters, in particular the solubility of the liquid crystal mixture in the polymer used for the matrix, do not unduly change with its addition.

[0420]

Embedded image A high nematic forming substance such as

In the case of liquid-crystal mixtures containing compounds of the formulas II to IV, the person skilled in the art can vary the relative amounts of these compounds in the mixture, for example to improve the birefringence. For mixtures having very high Δn, for example, formula II1,
Compounds of the formula II16, IV3 or IV4 can be used in particular, while for liquid-crystal mixtures with relatively low Δn values, for example, the compounds of the formula I
Compounds II1 to III3 are preferred. Of course, the person skilled in the art will be able to make a preferred choice from the compounds of the formula I without difficulty with regard to the desired Δn value. For mixtures having a relatively high or high Δn, for example, compounds of the formula Ig are generally preferred, while for liquid crystal mixtures of the invention having a relatively low or low Δn, two or more saturated rings Compounds of the system are generally particularly suitable.

In order to achieve a low threshold voltage, a liquid crystal mixture with a very high dielectric anisotropy Δε is generally required. Those skilled in the art will recognize from the group of compounds of the formula I, in particular the formulas Ia to Ii, that furthermore the formula II
To IV and a group of preferred component mixtures. To increase Δε, the person skilled in the art can, for example, add compounds of the formula II6 to the liquid-crystal mixture. These compounds are extremely strong dielectrically positive compounds. For example, the propyl homolog (alkyl = C ₃ H ₇ ) is Δε
= 50. One skilled in the art will select the concentration of such additives so that the liquid crystal mixture is most compatible with the particular embodiment of the electro-optic system. In particular, care is taken to affect the Δn and / or n ₀ and / or one or more further refractive indices of the liquid crystal in an acceptable and / or slight and / or negligible manner.

Those skilled in the art will recognize from the group of compounds of formula I, in particular formulas Ia-Ii, that the liquid crystal mixture is optimized for a particular application.
Furthermore, the properties of the liquid-crystal mixtures according to the invention can be modified for certain applications by optimizing them, if necessary, from the group of compounds of the formulas II to IV and the group of preferred component mixtures, and to optimize them within a certain range. be able to.

However, liquid crystals containing a compound of the formula I, in particular of the formulas Ia to Ii, and in particular a liquid crystal mixture containing one or more compounds of the formulas II to IV are used in the electro-optical liquid crystal system according to the invention. It is important that they are particularly suitable for Mixtures containing one or more of the preferred component mixtures are especially very suitable liquid-crystal mixtures.

The liquid-crystal mixtures according to the invention containing one or more compounds of the formula I, in particular of the formulas Ia to Ii, can be used without the other parameters of the mixture being simultaneously changed unduly and without the utility of the mixture in electro-optical systems. Also meant are "stable structure mixtures" which are particularly suitable for application to electro-optical systems, which can generally be optimized by the methods and / or additives described above for specific requirements without significant adverse changes. is there.

The liquid-crystal mixtures according to the invention are particularly suitable for use in electro-optical systems according to the preamble of claim 1. Thus, considerable commercial importance exists in the liquid crystals of the present invention and the electro-optical systems of the present invention.

The liquid-crystal mixtures according to the invention can be modified by further additives so that they can be used in all electro-optical systems according to the preamble of claim 1.

Additives of this kind are known to the person skilled in the art and are described in detail in the literature. Thus, for example, by adding a multicolor dye, a colored electro-optical system can be manufactured,
Alternatively, certain substances can be added to improve the temperature dependence of the dielectric anisotropy, optical anisotropy, viscosity and / or electro-optical parameters of the liquid crystal. Such substances are described, for example, in H. Kelker and R. Kelker. Hats
z), `` Handbook of Liquid Crystal
s) ", Chemical Publishers, Weinheim (1980), and
DE-OS 2,209,127,2,240,864,2,32
1,632,2,338,281,2,450,088,2,
637,430, 2,853,728 and 2,902,1
77.

An electro-optical liquid crystal system in which a polychromatic dye is added to a liquid crystal mixture in a range of 0 to 25% by weight, particularly 0 to 20% by weight, and more particularly 0 to 15% by weight is preferable.

Furthermore, as described, for example, in DE 4,007,039, chiral mesogenic or non-mesogenic compounds are added to the liquid-crystal mixtures according to the invention in order to increase the scattering in the opaque state and / or It can affect the slope of the electro-optic curve. The liquid crystal of the present invention preferably contains 0 to 15%, particularly 0 to 10% of a chiral additive.

The electro-optical liquid crystal system of the present invention can be switched by applying a DC or AC voltage.
However, it is preferred to use an AC voltage with an effective AC voltage amplitude of 1 to 24 volts and an AC voltage frequency of 10 Hz to 10 kHz. Amplitude of 2 to 220 volts and 20
Frequencies of up to 120 Hz are particularly preferred. It is very particularly preferred that the amplitude of the AC voltage is between 2 and 130 V.

The liquid-crystal mixtures which can be used according to the invention are prepared in a manner customary per se. In general, the desired amount of the components, which are used in small amounts, are conveniently dissolved in the main constituent components at an elevated temperature. It is also possible to mix solutions of these components in an organic solvent, such as acetone, chloroform or methanol, and to remove the solvent again after sufficient mixing, for example by distillation.

[0433]

The following examples illustrate the invention but do not limit it.

The symbols in the examples have the following meanings. K: crystalline solid S: smectic phase (indicating the type of phase), N: nematic phase, I: isotropic phase.

The number between the two symbols indicates the transition temperature in ° C. The indicated percentages are percentages by weight.

Example 1 a) An electro-optical liquid crystal system containing a liquid crystal mixture consisting of the following compounds: 14.4% p-trans-4-propylcyclohexylbenzonitrile; 11.2% p-trans-4- Butylcyclohexylbenzonitrile; 20% p-trans-4-pentylcyclohexylbenzonitrile; 12% p-trans-4-heptylcyclohexylbenzonitrile; 5.6% 4- (trans-4-pentylcyclohexyl)
-4%-(trans-4-propylcyclohexyl) biphenyl; 4.8% of 4-pentyl-4 "-cyanoterphenyl; 6.4% of trans-4-butylcyclohexylcarboxylic acid 4- (trans-4- Propylcyclohexyl) phenyl; 5.6% of 4- (trans-4-pentylcyclohexyl)
-4'-cyanobiphenyl; 20% of 1- (4- (4-pentylphenyl) phenyl)-
2- (3-fluoro-4-cyanophenyl) ethane.

B) The above-mentioned electro-optical liquid crystal system is manufactured by the following various methods 1.1 to 1.3 and 2. 1. Microdroplet matrix system NOA65 [Norland] adhesive, which can cure the liquid crystal mixture of 1.1a) by UV irradiation
And stir at room temperature in a ratio of 1.6: 1 until a clear solution is obtained. This solution is introduced between two transparent glass support plates provided with an electrode layer together with a spacer (20 μm). The glass support plate is pressed from both sides to obtain a uniform film with a thickness of 20 μm. This is cured by UV irradiation for one minute.

The liquid crystal mixture of 1.2a) was epicoated (Epicoat).
kote) 828 and Capcure 3-800
[Miller Stepheen Company
nson Company) at room temperature in a ratio of 1: 1: 1 until a clear solution is obtained. The stirring time should be as short as possible since the solution will already harden at room temperature after about 1/2 hour. This solution is introduced between two transparent glass support plates provided with an electrode layer together with a spacer (20 μm). The glass support plate is pressed from both sides to obtain a uniform film with a thickness of 20 μm. The film can be heated to a temperature of up to 100 ° C. to accelerate the curing process.

5 g of the liquid crystal mixture of 1.3a) was added to 20% of PVA
Stir at 2000 rpm for 2 minutes at room temperature with 15 g of aqueous solution. The obtained solution is degassed for 24 hours, and applied together with a spacer (20 μm) on a glass support plate provided with an electrode layer to form a thin layer. After drying the assembly at 85 ° C. for 1 hour, a second glass support plate provided with an electrode layer is applied thereon to obtain a uniform film having a thickness of 20 μm. The system thus obtained is dried at 85 ° C. for a further 24 hours. 2. Using the liquid crystal mixture of the network structure system a) as a polymerizable compound as trimethylolpropane triacrylate and 2-hydroxy-2-methyl-1-phenylpropan-1-one as a photopolymerization initiator [Darocure 1173; Darmstadt, product of E. Merck] at a ratio of 80: 19.8: 0.2. This is introduced together with a spacer having a thickness of 20 μm between two glass support plates provided with an electrode layer. In order to cure the polymer, the resulting system was irradiated with a radiation field of a halogen lamp (70 W / cm) at a constant speed (3 m
/ Min).

Method b) The electro-optical systems produced according to 1.1 to 1.3 and 2 are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and especially low threshold voltages. I do.

Example 2 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters: 9% p-trans-4-propylcyclohexylbenzonitrile; 7% p -Trans-4-butylcyclohexylbenzonitrile; 12.5% p-trans-4-pentylcyclohexylbenzonitrile; 7.5% p-trans-4-heptylcyclohexylbenzonitrile; 3.5% 4- ( Trans-4-pentylcyclohexyl)
-4 '-(trans-4-propylcyclohexyl) biphenyl; 8% of 4-pentyl-4 "-cyanoterphenyl; 4% of trans-4-butylcyclohexylcarboxylic acid 4
-(Trans-4-propylcyclohexyl) phenyl; 11% of 4- (trans-4-pentylcyclohexyl)-
4'-cyanobiphenyl; 3.5% of 1- (4- (4-pentylphenyl) phenyl)
--2- (4-cyanophenyl) ethane; 3.5% of 1- (4- (4-pentylphenyl) phenyl)
3.5-% of 2- (3-fluoro-4-cyanophenyl) ethane; 3.5% of 1- (4- (4-propylphenyl) phenyl)
2.5-% of 4-propyl-4'-cyanobiphenyl; 7.5% of 4-ethyl-4'-cyanobiphenyl; 17% of 4- Pentyl-4'-cyanobiphenyl.

Clearing point Tc = 93 ° C. Viscosity η = 38 mm ² / sec (20 ° C.) Optical anisotropy Δn = 0.20 (20 ° C., 589 nm) Dielectric anisotropy Δε = 15.2 (20 ° C., 1 kHz) b) The electro-optical liquid crystal system is manufactured by the method described in Examples 1, 1.1 to 1.3 and 2.

Reference Example 1 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters: 11% of 4-ethyl-4'-cyanobiphenyl; 5% of 4- Propyl-4'-cyanobiphenyl; 10% 4-heptyl-4'-cyanobiphenyl; 37% 4-pentyl-4'-cyanobiphenyl; 12% 4-octoxy-4'-cyanobiphenyl; 15% 4-pentyl 3 ", 5" -difluoro-4 "-cyanoterphenyl; 10% of 4-pentyl 3 ', 5'-difluoro-4" -cyanoterphenyl.

Dielectric Anisotropy Δε = 20.0 (20 ° C., 1 kHz) Optical Anisotropy Δn = 0.233 (20 ° C., 589 nm) b) The above electro-optical liquid crystal system was used in Examples 1, 1.1 to 1 .3 and 2.

Reference Example 2 a) Electro-optical liquid crystal system containing a liquid crystal mixture consisting of the following compounds: 28% of 2- (4-cyanophenyl) -5-ethylpyridine; 28% of 2- (4-cyanophenyl ) -5-propylpyridine; 29% of 2- (4-cyanophenyl) -5-pentylpyridine; 15% of 4-pentyl 3 ", 5" -difluoro-4 "-cyanoterphenyl; b) electro-optic as described above. A liquid crystal system is produced by the method described in Example 1, b).

Example 3 a) Electro-optical liquid crystal system containing a liquid crystal mixture consisting of the following compounds: 19% of 2- (4-cyanophenyl) -5-ethylpyrimidine; 19% of 2- (4-cyanophenyl ) -5-Butylpyrimidine; 19% 2- (4-cyanophenyl) -5-pentylpyrimidine; ro-4-cyanophenyl) ethane; 12% 4-pentyl-4'-cyanobiphenyl.

B) The electro-optical liquid crystal system described in Example 1, b)
It is manufactured by the method described in (1).

Reference Example 3 a) Electro-optical liquid crystal system containing a liquid crystal mixture consisting of the following compounds: 20% of 2- (4-cyanophenyl) -5-ethylpyrimidine; 20% of 2- (4-cyanophenyl) ) -5-propylpyrimidine; 20% of 2- (4-cyanophenyl) -5-pentylpyrimidine; 20% of 4-pentyl 3 ", 5" -difluoro-4 "-cyanoterphenyl; 20% of 4- Pentyl-4'-cyanobiphenyl.

B) The electro-optical liquid crystal system described in Example 1, b)
It is manufactured by the method described in (1).

Example 4 a) Electro-optical liquid crystal system containing a liquid crystal mixture consisting of the following compounds: 20% of 1- (trans-4- (trans-4-propylcyclohexyl) cyclohexyl-2- (3-fluoro-) 4-
Cyanophenyl) ethane; 14.4% p-trans-4-propylcyclohexylbenzonitrile; 11.2% p-trans-4-butylcyclohexylbenzonitrile; 20% p-trans-4-pentylcyclohexylbenzonitrile 12% p-trans-4-heptylcyclohexylbenzonitrile; 5.6% 4- (trans-4-pentylcyclohexyl)
4.8% of 4-pentyl-4 "-cyanoterphenyl; 6.4% of 4- (trans-4-propylcyclohexylcarboxylate) 4- (trans-4-propylcyclohexyl) biphenyl; Cyclohexyl) phenyl; 5.6% of 4- (trans-4-pentylcyclohexyl)
-4'-Cyanobiphenyl.

B) The electro-optical liquid-crystal systems produced by the method described in Example 1 b) are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and especially low threshold voltages. .

Reference Example 4 a) A liquid crystal mixture consisting of the following compounds has the following physical data: 43% of 4-pentyl-4'-cyanobiphenyl; 17% of 4-propoxy-4'- 13% 4-pentoxy-4'-cyanobiphenyl; 17% 4-octoxy-4'-cyanobiphenyl; 10% 4-pentyl-4 "-cyanotelphenyl.

Birefringence Δn = 0.246 (20 ° C., 589 nm) Threshold voltage V [90.0.20] = 1.44 V The threshold voltage has a cell spacing of d = 7 μm, and is between the orthogonal polarizers. The measurement was performed in an installed TN cell (twist angle Ψ = π / 4).

B) A liquid crystal mixture comprising the following compounds has the following physical properties.

30% of 4-pentyl-4'-cyanobiphenyl; 15% of 4-ethyl-4'-cyanobiphenyl; 20% of 4- (propylphenyl) -3-fluoro-4'-
10% 4-propyl-2-fluoro-4'-cyanobiphenyl; 15% 4-pentyl-2-fluoro-4'-cyanobiphenyl; 10% 4-pentyl-4 "-fluoro-4. ″ -Cyanoterphenyl.

Birefringence Δn = 0.246 Threshold voltage V [90.0.20] = 1.26 V The threshold voltage has a cell spacing of d = 7 μm, and a TN cell placed between orthogonal polarizers ( The measurement was performed at a twist angle Ψ = π / 4).

The advantageous properties of the mixtures according to the invention are described in Example 4 a).
It is clear from the comparison of the results of (b) and (b).

C) An electro-optical system was produced by the method described in Example 1b) using a mixture of Reference Example 4 a) and b). Reference Example 4 The system produced with the liquid crystal mixture of b) is a reference example.
4 It has advantageous properties over systems made with the mixture of a), and is characterized by a particularly low threshold voltage.

Reference Example 5 a) A liquid crystal mixture consisting of the following compounds has the following physical properties: 20% of 4- (trans-4-pentylcyclohexyl)
Benzonitrile; 15% 4-pentyl-4'-cyanobiphenyl; 15% 4-ethyl-4'-cyanoterphenyl; 5% 4-pentyl-4 "-cyanoterphenyl; 15% 4- ( 4-propylphenyl) -3-fluoro-
10% 4-propyl-2-fluoro-4'-cyanobiphenyl; 15% 4-pentyl-2-fluoro-4'-cyanobiphenyl; 5% 4- (trans-4- Pentylcyclohexyl)
-4'-cyanobiphenyl.

Birefringence Δn = 0.218 (20 ° C., 589 nm) Ordinary refractive index n0 = 1.522 (20 ° C., 589 nm) Dielectric anisotropy Δε = 16.71 (20 ° C., 1 kHz) Threshold Voltage V [90.0.20] = 1.33 V The threshold voltage was measured with a TN cell (twist angle ψ = π / 4) having a cell spacing of d = 7 μm and placed between orthogonal polarizers.

B) The electro-optical systems produced by the method described in Example 1 b) are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and especially low threshold voltages.

Reference Example 6 a) A liquid crystal mixture consisting of the following compounds has the following physical properties: 12% of 4-ethyl-4-cyanobiphenyl; 4% of 4-propyl-4-cyanobiphenyl 29.6% 4-pentyl-4-cyanobiphenyl; 8.8% 4-propoxy-4-cyanobiphenyl; 8.0% 4-pentyl-4 "-cyanoterphenyl; 20.0% 4- (4-propylphenyl) -3-fluoro-4'-cyanobiphenyl; 5.6% 4- (4-cyanophenyl) phenyl 4- (4-heptylphenyl) phenylcarboxylate; 12% 4- (Trans-4-pentylcyclohexyl-4'-cyanobiphenyl.

Birefringence Δn = 0.286 (20 ° C., 589 nm) Ordinary light refractive index n ₀ = 1.530 (20 ° C., 589 nm) Dielectric anisotropy Δε = 13.5 (20 ° C., 1 kHz) Threshold voltage V [90.0.20] = 1.66 V Absorption coefficient γ = 1.629 (λ: 350 nm) γ = 0.130 (λ: 360 nm) γ = 0.006 (λ: 370 nm) Clearing point N 113 I extinction coefficient is given by the formula

[0464]

(Equation 1) (Where A is the absorbance, l is the thickness of the liquid crystal layer where the light crosses, in cm, and CW is 100 ml of solution
(The mass of the liquid crystal expressed in grams per unit).

The threshold voltage was measured as shown in Reference Example 5 a).

B) The electro-optical systems produced by the method described in Example 1 b) are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and especially low threshold voltages.

Reference Example 7 a) A liquid crystal mixture consisting of the following compounds has the following physical properties: 14% of 4-ethyl-4-cyanobiphenyl; 5% of 4-propyl-4-cyanobiphenyl 33.0% 4-pentyl-4-cyanobiphenyl; 12.0% 4-propoxy-4-cyanobiphenyl; 10.0% 4-pentyl-4 "-cyanotelphenyl; 23.0% 4- (4-propylphenyl) -3-fluoro-4'-cyanobiphenyl; 3.0% 4- (4-cyanophenyl) phenyl 4- (4-heptylphenyl) phenylcarboxylate.

Birefringence Δn = 0.287 (20 ° C., 589 nm) Ordinary ray refractive index n ₀ = 1.533 (20 ° C., 589 nm) Dielectric anisotropy Δε = 14.1 (20 ° C., 1 kHz) Threshold voltage V [90.0.20] = 1.60 V Clearing point N 96 I The threshold voltage was measured as shown in Reference Example 5 a).

B) The electro-optical systems produced by the method described in Example 1 b) are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and especially low threshold voltages.

Reference Example 8 a) A liquid crystal mixture consisting of the following compounds has the following physical properties: 35.0% of 4-pentyl-4'-cyanobiphenyl; 12.0% of 4-propoxy 14.0% of 4-pentoxy-4'-cyanobiphenyl; 6.0% of 4-pentyl-4 "-cyanoterphenyl; 23.0% of 4- (4-propylphenyl ) -3-Fluoro-4'-cyanobiphenyl; 3.0% of 4- (4-cyanophenyl) phenyl 4- (4-heptylphenyl) phenylcarboxylate; 7.0% of 4-octoxy-4'cyano Biphenyl.

Birefringence Δn = 0.280 (20 ° C., 589 nm) Ordinary refractive index n ₀ = 1.527 (20 ° C.) Dielectric anisotropy Δε = 13.0 (20 ° C., 1 kHz) Threshold voltage V [90.0.20] = 1.71 V Clearing point N 97 I The threshold voltage was measured as shown in Reference Example 5 a).

B) The electro-optical systems produced by the method described in Example 1 b) are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and in particular a low threshold voltage.

Reference Example 9 a) A liquid crystal mixture consisting of the following compounds has the following physical properties: 32.0% of 4-pentyl-4'-cyanobiphenyl; 12.0% of 4-propoxy 13.0% of 4-pentoxy-4'-cyanobiphenyl; 8.0% of 4-pentyl-4 "-cyanotelphenyl; 22.0% of 4- (4-propylphenyl ) -4-Fluoro-4'-cyanobiphenyl; 3.0% of 4- (4-cyanophenyl) phenyl 4- (4-heptylphenyl) phenylcarboxylate; 5.0% of 4-octoxy-4'- Cyanobiphenyl; 5.0% of 4- (trans-4-pentylcyclohexyl) -4'-cyanobiphenyl.

Birefringence Δn = 0.284 (20 ° C., 589 nm) Ordinary refractive index n ₀ = 1.526 (20 ° C., 589 nm) Clearing point N 108 I b) Produced by the method described in Example 1b) The resulting electro-optical system is characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and especially low threshold voltages.

Reference Example 10 a) A liquid crystal mixture consisting of the following compounds has the following physical properties: 33.0% of 4-pentyl-4'-cyanobiphenyl; 12.0% of 4-propoxy 14.0% of 4-pentoxy-4'-cyanobiphenyl; 10.0% of 4-pentyl-4 "-cyanotelphenyl; 23.0% of 4- (4-propylphenyl ) -3-Fluoro-4'-cyanobiphenyl; 3.0% 4- (4-cyanophenyl) phenyl 4- (4-heptylphenyl) phenylcarboxylate; 5.0% 4-octoxy-4'cyano Biphenyl.

Birefringence Δn = 0.288 (20 ° C., 589 nm) Ordinary refractive index n ₀ = 1.528 (20 ° C., 589 nm) Clearing point N 105 I b) Produced by the method described in Example 1b) The resulting electro-optical system is characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and especially low threshold voltages.

Reference Example 11 a) A liquid crystal mixture consisting of the following compounds has the following physical properties: 30.0% of 4-hexyl-4'-cyanobiphenyl; 10.0% of 4-pentoxy 7.0% 4-octoxy-4'-cyanobiphenyl; 5.0% 4-pentyl-4 "-cyanotelphenyl; 15.0% 4- (4-propylphenyl ) -3-Fluoro-4'-cyanobiphenyl; 5.0% of 4- (trans-4-pentylcyclohexyl) benzoyl tolyl; 8.0% of 1-propoxy-trans-4- (trans-4-propyl) Cyclohexyl) cyclohexane; 20.0% 4- (trans-4-pentylcyclohexyl) -4′-cyanobiphenyl.

Birefringence Δn = 0.2293 (20 ° C., 589 nm) Ordinary refractive index n ₀ = 1.5151 (20 ° C., 589 nm) Clearing point N 102 I b) Produced by the method described in Example 1b) The resulting electro-optical system is characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and especially low threshold voltages.

Reference Example 12 a) A liquid crystal mixture consisting of the following compounds has the following physical properties: 32.0% of 4-pentyl-4'-cyanobiphenyl; 12.0% of 4-propoxy 13.0% of 4-pentoxy-4'-cyanobiphenyl; 6.0% of 4-pentyl-4 "-cyanotelphenyl; 23.0% of 4- (4-propylphenyl ) -3-Fluoro-4'-cyanobiphenyl; 3.0% of 4- (4-cyanophenyl) phenyl 4- (4-heptylphenyl) phenylcarboxylate; 5.0% of 4-octoxy-4'- Cyanobiphenyl; 6.0% of 4- (trans-4-pentylcyclohexyl) -4'-cyanobiphenyl.

Birefringence Δn = 0.283 (20 ° C., 589 nm) Ordinary refractive index n ₀ = 1.564 (20 ° C., 589 nm) Dielectric anisotropy Δε = 12.8 (20 ° C., 1 kHz) Threshold voltage V [90.0.20] = 1.73V Clearing point N 108 I The threshold voltage was measured as described in Example 9a).

B) The electro-optical systems produced by the method described in Example 1 b) are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and in particular a low threshold voltage.

Reference Example 13 a) A liquid crystal mixture consisting of the following compounds has the following physical properties: 10.0% of 4-pentoxy-4'-cyanobiphenyl; 7.0% of 4-octoxy 31.0% of 4-hexyl-4'-cyanobiphenyl; 12.0% of 4- (trans-4-pentylcyclohexyl) benzonitrile; 20.0% of 4- (trans- 4-pentylcyclohexyl) -4′-cyanobiphenyl; 15.0% of 4- (4-propylphenyl) -3-fluoro-4′cyanobiphenyl; 5.0% of 4-pentyl-4 ″ -cyanoterphenyl .

Birefringence Δn = 0.2373 (20 ° C., 589 nm) Ordinary refractive index n ₀ = 1.5183 (20 ° C., 589 nm) Dielectric anisotropy Δε = 14.0 Clearing point N 105 Ib) The electro-optical systems produced by the method described in Example 1b) are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and especially low threshold voltages.

Reference Example 14 a) A liquid crystal mixture consisting of the following compounds has the following physical properties: 20.0% of 4- (trans-4-pentylcyclohexyl) benzonitrile; 15.0% 4- (trans-4-propylcyclohexyl) benzonitrile; 10.0% of 4- (trans-4-butylcyclohexyl) benzonitrile; 10.0% of 4-pentyl-4'-cyanobiphenyl; 10.0% 4-ethyl-4'-cyanobiphenyl; 7.0% of 4-propyl-4-cyanobiphenyl; 10.0% of 4- (trans-4-pentylcyclohexyl) -4'-cyanobiphenyl; 10.0 % Of 4- (4-propylphenyl) -3-fluoro-4'-cyanobiphenyl; 8.0% of 4-pentyl-4 "-cyanoterphenyl.

Birefringence Δn = 0.0242 (20 ° C., 589 nm) Ordinary refractive index n ₀ = 1.5132 (20 ° C., 589 nm) Dielectric anisotropy Δε = 14.8 (20 ° C., 1 kHz) Transparent Point N 81 I b) The electro-optical system produced by the method described in Example 1 b) is characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and especially low threshold voltages. .

Reference Example 15 a) A liquid crystal mixture consisting of the following compounds has the following physical properties: 30.0% of 4-pentyl-4'-cyanobiphenyl; 15.0% of 4-ethyl -4'-cyanobiphenyl; 20.0% of 4- (4-propylphenyl) -3-fluoro-4'-cyanobiphenyl; 10.0% of 4-propyl-2-fluoro-4'-cyanobiphenyl; 15.0% 4-pentyl-2-fluoro-4'-cyanobiphenyl; 10.0% 4-pentyl-3 "-fluoro-4" -cyanoterphenyl.

Birefringence Δn = 0.246 (20 ° C., 589 nm) Threshold voltage V [90.0.20] = 1.26 V Clearing point N 62 I The threshold voltage was as shown in Reference Example 5 a). Was measured.

B) The electro-optical systems produced by the method described in Example 1 b) are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and especially low threshold voltages.

Example 5 a) A liquid crystal mixture consisting of the following compounds has the following physical properties: 25.0% of 4-pentyl-4'-cyanobiphenyl; 15.0% of 4-ethyl -1'-cyanobiphenyl; 18.0% of 4- (4-propylphenyl) -3-fluoro-4'-cyanobiphenyl; 10.0% of 4-propyl-2-fluoro-4'-cyanobiphenyl; 10.0% of 4-pentyl-2-fluoro-4'-cyanobiphenyl; 10.0% of 4-pentyl-3 ", 5" -difluoro-
4% -cyanoterphenyl; 6.0% of 4-nonyl-3 "-fluoro-4"-cyanoterphenyl; 6.0% of 1- [trans-4- (trans-4-propylcyclohexyl) cyclohexyl] -2- [4-
(4-cyanophenyl) phenyl] ethane.

Birefringence Δn = 0.258 (20 ° C., 589 nm) Threshold voltage V [90.0.20] = 1.33 V Dielectric anisotropy Δε = 19.7 (20 ° C., 1 kHz) Clearing point The N 82 I threshold voltage was measured as described in Reference Example 5 a).

B) The electro-optical systems produced by the method described in Example 1 b) are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and especially low threshold voltages.

Reference Example 16 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters: 14.4% p-trans-4-propylcyclohexylbenzonitrile; 2% p-trans-4-butylcyclohexylbenzonitrile; 20% p-trans-4-pentylcyclohexylbenzonitrile; 12% p-trans-4-heptylcyclohexylbenzonitrile; 5.6% 4- ( Trans-4-pentylcyclohexyl) -4 '-(trans-4-propylcyclohexyl) biphenyl; 4.8% of 4-pentyl-4 "-cyanoterphenyl; 6.4% of trans-4-butylcyclohexylcarboxylic acid 4- (trans-4-propylcyclohexyl) phenyl; 5.6 Of 4- (trans-4-pentylcyclohexyl) -4'-cyanobiphenyl; 20% of the 2- (3-fluoro-4-cyanophenyl) -
5-pentylpyrimidine.

Viscosity η = 34 mm ² / sec (20 ° C.) Optical anisotropy Δn = 0.15 (20 ° C., 589 nm) Dielectric anisotropy Δε = 17.8 (20 ° C., 1 kHz) b) Examples The electro-optical systems produced according to the method described under 1b) are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and especially low threshold voltages.

Reference Example 17 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters: 14.4% p-trans-4-propylcyclohexylbenzonitrile; 2% p-trans-4-butylcyclohexylbenzonitrile; 20% p-trans-4-pentylcyclohexylbenzonitrile; 12% p-trans-4-heptylcyclohexylbenzonitrile; 5.6% 4- ( Trans-4-pentylcyclohexyl) -4 '-(trans-4' (trans-4-propylcyclohexyl) biphenyl; 4.8% of 4-pentyl-4 "-cyanoterphenyl; 6.4% of trans-4 4- (trans-4-propylcyclohexyl) butyl butylcyclohexylcarboxylate Alkylsulfonyl; 5.6% 4- (trans-4-pentylcyclohexyl) -4'-cyanobiphenyl; 20% of the 2- (4-cyanophenyl) -5-propyl-pyridine.

Clearing point TC = 80 ° C. Viscosity η = 33 mm ² / sec (20 ° C.) Optical anisotropy Δn = 0.16 (20 ° C., 589 nm) Dielectric anisotropy Δε = 15.5 (20 ° C. 1 kHz) b) The electro-optical systems produced by the method described in Example 1 b) are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and especially low threshold voltages.

Reference Example 18 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters: 14.5% p-trans-4-propylcyclohexylbenzonitrile; 2% p-trans-4-butylcyclohexylbenzonitrile; 20% p-trans-4-pentylcyclohexylbenzonitrile; 12% p-trans-4-heptylcyclohexylbenzonitrile; 5.6% 4- ( Trans-4-pentylcyclohexyl) -4 '-(trans-4-propylcyclohexyl) biphenyl; 6.4% 4- (trans-4-propylcyclohexyl) phenyl trans-4-butylcyclohexylcarboxylate; 5.6% 4- (trans-4-pentylcyclohexyl) -4 '-Cyanobiphenyl; 4.8% of 4-pentyl-4 "-cyanoterphenyl; 20% of 2- (4-cyanophenyl) -5-pentylpyrimidine.

Clearing point TC = 82 ° C. Viscosity η = 34 mm ² / sec (20 ° C.) Optical anisotropy Δn = 0.16 (20 ° C., 589 nm) Dielectric anisotropy Δε = 16.1 (20 ° C., 1 kHz) b) The electro-optical systems produced by the method described in Example 1 b) are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and especially low threshold voltages.

Reference Example 19 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters: 17% of 1-difluoromethoxy-2-fluoro-4-
[Trans-4- (trans-4-ethylcyclohexyl) cyclohexyl] benzene; 17% of 1-difluoromethoxy-2-fluoro-4-
[Trans-4- (trans-4-butylcyclohexyl) cyclohexyl] benzene; 17% of 1-difluoromethoxy-2-fluoro-4-
[Trans-4- (trans-4-pentylcyclohexyl) cyclohexyl] benzene; 11% of 1-difluoromethoxy-4- [trans-4
-(Trans-4-pentylcyclohexyl) cyclohexyl] benzene; 6% of 1- (trans-4-propylcyclohexyl)
-2- (4-difluoromethoxyphenyl) ethane; 6% of 1- (trans-4-pentylcyclohexyl)
-2- (4-difluoromethoxyphenyl) ethane; 6% of 1-difluoromethoxy-4- (trans-4-
Pentylcyclohexyl) benzene; 8% 4-propyl-4'-difluoromethoxybiphenyl; 12% 4- (trans-4-propylcyclohexyl) -4'-difluoromethoxybiphenyl.

Clearing point TC = 87 ° C. Viscosity η = 19 mm ² / sec (20 ° C.) Optical anisotropy Δn = 0.0985 (20 ° C., 589 nm) Dielectric anisotropy Δε = 6.3 (20 ° C. 1 kHz) b) An electro-optical liquid crystal system is manufactured by the method described in Examples 1b), 1.1 to 1.3 and 2.

Method b) The electro-optical systems prepared according to 1.1 to 1.3 and 2 have good manufacturability, a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, low threshold voltages And good contrast as well as particularly high stability.

Reference Example 20 a) Electro-optical liquid crystal system containing a liquid crystal mixture consisting of the following compounds: 20% of 2- (4-cyanophenyl) -5-propylpyridine; 20% of 2- (4-cyanophenyl ) -5-butylpyridine; 20% 2- (4-cyanophenyl) -5-pentylpyridine; 25% 4-pentyl-4'-cyanobiphenyl; 15% 4-pentyl-4 "-cyanoterphenyl .

B) The electro-optical systems produced by the method described in Example 1 b) are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and especially low threshold voltages.

Example 6 a) An electro-optical liquid crystal system containing a liquid crystal mixture consisting of the following compounds: 20% of 2- (4-cyanophenyl) -5-propylpyridine; 20% of 2- (4-cyanophenyl ) -5-butylpyridine; 20% 2- (4-cyanophenyl) -5-pentylpyridine; 20% 4-pentyl-2-fluoro-4'-cyanobiphenyl; 10% 1- (4- ( 4-pentylphenyl) phenyl) -2- (3-fluoro-4-cyanophenyl) ethane; 10% of 4-pentyl-4'-cyanoterphenyl.

B) The electro-optical systems produced by the method described in Example 1 b) are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and especially low threshold voltages.

Example 7 a) An electro-optical liquid crystal system containing a liquid crystal mixture consisting of the following compounds: 30% of 2- (4-cyanophenyl) -5-propylpyridine; 30% of 2- (4-cyanophenyl ) -5-butylpyridine; 20% 2- (4-cyanophenyl) -5-pentylpyridine; 10% 2- (4-cyanophenyl) -5- (4-pentylphenyl) pyridine; 10% 1 -(4- (5-pentylpyridinyl-2) phenyl) -2- (3-fluoro-4-cyanophenyl)
Ethane.

B) The electro-optical systems produced by the method described in Example 1 b) are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and in particular a low threshold voltage.

Example 8 a) Electro-optical liquid crystal system containing a liquid crystal mixture consisting of the following compounds: 30% 2- (4-cyanophenyl) -5-propylpyridine; 30% 2- (4-cyanophenyl) ) -5-butylpyridine; 20% 2- (4-cyanophenyl) -5-pentylpyridine; 10% 1- (4- (4-pentylphenyl) phenyl) -2- (3-fluoro-4- Cyanophenyl) ethane; 10% of 1- (4-pentylphenyl) -2- (4-
(4-cyanophenyl) phenyl) ethane.

B) The electro-optical systems produced by the method described in Example 1 b) are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and especially low threshold voltages.

Reference Example 21 a) Electro-optical liquid crystal system containing a liquid crystal mixture consisting of the following compounds: 20% of 2- (4-cyanophenyl) -5-ethylpyrimidine; 20% of 2- (4-cyanophenyl ) -5-propylpimiridine; 20% 2- (4-cyanophenyl) -5-pentylpyrimidine; 20% 4-pentyl-3 ", 5" -difluoro-4 "
-Cyanotelphenyl; 20% of 2-fluoro-4-pentyl-4'-cyanobiphenyl.

B) The electro-optical systems produced by the method described in Example 1 b) are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and especially low threshold voltages.

Reference Example 22 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters: 10.0% of 2- (4-cyanophenyl) -5-propyl- 1,3-dioxane; 15.0% of 2- (4-cyanophenyl) -5-butyl-1,3-dioxane; 15.0% of 2- (4-cyanophenyl) -5-pentyl-1, 3-dioxane; 20.0% of 4- (trans-4-propylcyclohexyl) benzonitrile; 15.0% of 4- (trans-4-pentylcyclohexyl) benzonitrile; 10.0% of 4- (trans- 4-heptylcyclohexyl) benzonitrile; 5.0% of 4- (trans-4-propylcyclohexyl) -4 '-(trans-4-propylcyclohexyl) bif 5.0% of 4- (trans-4-pentylcyclohexyl) -4 ′-(trans-4-pentylcyclohexyl) biphenyl; 5.0% of 4- (trans-4-pentylcyclohexyl) -4′- (Trans-4-propylcyclohexyl) biphenyl.

Clearing point TC = 76 ° C. Viscosity η = 34 mm ² / sec (20 ° C.) Optical anisotropy Δn = 0.131 (20 ° C., 589 nm) Dielectric anisotropy Δε = 17 (1 kHz, 20 ° C.) b) The electro-optical systems produced by the method described in Example 1b) are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and especially low threshold voltages.

Reference Example 23 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters: 15.0% of 2- (4-cyanophenyl) -5-propyl- 1,3-dioxane; 10.0% of 2- (4-cyanophenyl) -5-butyl-1,3-dioxane; 15.0% of 2- (4-cyanophenyl) -5-pentyl-1, 15.0% 2- (4-cyanophenyl) -5-propylpyridine; 15.0% 2- (4-cyanophenyl) -5-butylpyridine; 15.0% 2- ( 4-cyanophenyl) -5-pentylpyridine; 5.0% of 4- (trans-4-propylcyclohexyl) -4 '-(trans-4-propylcyclohexyl) biphenyl; 5.0% of 4- (tran -4-pentylcyclohexyl) -4 '-(trans-4-pentylcyclohexyl) biphenyl; 5.0% of 4- (trans-4-pentylcyclohexyl) -4'-(trans-4 '-(trans-4- Propylcyclohexyl) biphenyl.

Clearing point TC = 68 ° C. Viscosity η = 45 mm ² / sec (20 ° C.) Optical anisotropy Δn = 0.131 (20 ° C., 589 nm) Dielectric anisotropy Δε = 17 (1 kHz, 20 ° C.) b) The electro-optical systems produced by the method described in Example 1b) are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and especially low threshold voltages.

Reference Example 24 a) Electro-optical liquid crystal system containing a liquid crystal mixture consisting of the following compounds and having the following physical parameters: 15% of 2- (4-cyanophenyl) -5-propyl-
1,3-dioxane; 15% of 2- (4-cyanophenyl) -5-butyl-
1,3-dioxane; 15% of 2- (4-cyanophenyl) -5-pentyl-
1,3-dioxane; 20% of 4-pentyl-4'-cyanobiphenyl; 20% of 4'-heptyl-4'-cyanobiphenyl; 5% of 4- (trans-4-propylcyclohexyl)
-4 '-(trans-4-propylcyclohexyl) biphenyl; 5% of 4- (trans-4-pentylcyclohexyl)
-4 '-(trans-4-pentylcyclohexyl) biphenyl; 5% of 4- (trans-4-pentylcyclohexyl)
-4 '-(trans-4-propylcyclohexyl) biphenyl.

Clearing point TC = 72 ° C. Viscosity η = 38 mm ² / sec (20 ° C.) Optical anisotropy Δn = 0.166 (589 nm, 20 ° C.) Dielectric anisotropy Δε = 20 (1 kHz, 20 ° C.) b) The electro-optical systems produced by the method described in Example 1b) are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and especially low threshold voltages.

Reference Example 25 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters: 10% of 2- (4-cyanophenyl) -5-propyl-
1,3-dioxane; 10% of 2- (4-cyanophenyl) -5-butyl-
1,3-dioxane; 15% of 2- (4-cyanophenyl) -5-pentyl-
1,3-dioxane; 5% of 2- (4-cyanophenyl) -5-pentylpyrimidine; 10% of 2- (4-cyanophenyl) -5-heptylpyrimidine; 15% of 4- (trans-4- Propylcyclohexyl) benzonitrile; 10% 4- (trans-4-pentylcyclohexyl) benzonitrile; 10% 4- (trans-4-heptylcyclohexyl) benzonitrile; 5% 4- (trans-4-propylcyclohexyl) )
-4 '-(trans-4-propylcyclohexyl) biphenyl; 5% of 4- (trans-4-pentylcyclohexyl)
-4 '-(trans-4-propylcyclohexyl) biphenyl; 5% of 4- (trans-4-pentylcyclohexyl)
-4 '-(trans-4-propylcyclohexyl) biphenyl.

Clearing point TC = 76 ° C. Viscosity η = 38 mm ² / sec (20 ° C.) Optical anisotropy Δn = 0.15 (589 nm, 20 ° C.) Dielectric anisotropy Δε = 21 (1 kHz, 20 ° C.) b) The electro-optical systems produced by the method described in Example 1b) are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and especially low threshold voltages.

Example 9 a) An electro-optical liquid crystal system containing a liquid crystal mixture consisting of the following compounds: 20% of 1- (4- (4-pentylphenyl) phenyl) -2- (4-cyanophenyl) ethane; 14.4% p-trans-4-propylcyclohexylbenzonitrile; 11.2% p-trans-4-butylcyclohexylbenzonitrile; 20% p-trans-4-pentylcyclohexylbenzonitrile; 12% p -Trans-4-heptylcyclohexylbenzonitrile; 5.6% of 4- (trans-4-pentylcyclohexyl) -4 '-(trans-4-propylcyclohexyl) biphenyl; 4.8% of 4-pentyl-4 " 6.4% of trans-4-butylcyclohexylcarboxylic acid 4- (tolane; 4-propyl) phenyl; 5.6% 4- (trans-4-pentylcyclohexyl) -4'-cyanobiphenyl.

B) The electro-optical systems produced by the method described in Example 1 b) are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and in particular a low threshold voltage.

Example 10 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters: 14.4% p-trans-4-propylcyclohexylbenzonitrile; 2% p-trans-4-butylcyclohexylbenzonitrile; 20% p-trans-4-pentylcyclohexylbenzonitrile; 12% p-trans-4-heptylcyclohexylbenzonitrile; 5.6% 4- ( Trans-4-pentylcyclohexyl) -4 '-(trans-4-propylcyclohexyl) biphenyl; 4.8% of 4-pentyl-4 "-cyanoterphenyl; 6.4% of trans-4-butylcyclohexylcarboxylic acid 4- (trans-4-propylcyclohexyl) phenyl; 5.6 Of 4- (trans-4-pentylcyclohexyl) -4'-cyanobiphenyl; 20% 1- (trans-4-pentylcyclohexyl) -2- (4-cyanophenyl) ethane.

Clearing point TC = 80 ° C. Viscosity η = 29 mm ² / sec (20 ° C.) Optical anisotropy Δn = 0.14 (20 ° C., 589 nm) Dielectric anisotropy Δε = 11.8 (20 ° C. 1 kHz) b) The electro-optical system produced by the method described in Example 1 b) has good manufacturability, a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, as well as particularly low threshold voltages and It features high contrast.

Reference Example 26 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters: 21.2% of 2- (4-cyanophenyl) -5-propylpyridine 21.2% 2- (4-cyanophenyl) -5-butylpyridine; 21.2% 2- (4-cyanophenyl) -5-pentylpyridine; 21.2% 2- (4-cyano) Phenyl) -5- (4-
5.0% 4-propoxy-4'-fluorotolan; 5.0% 4-butoxy-4'-fluorotolan; 5.0% 4-pentoxy-4'-fluorotolan.

Clearing point TC = 75 ° C. Viscosity η = 58 mm ² / sec (20 ° C.) Optical anisotropy Δn = 0.2627 (20 ° C., 589 nm) Ordinary ray refractive index n0 = 1.5277 (20 ° C., 589 nm) B) Dielectric anisotropy Δε = 22.6 (20 ° C., 1 kHz) b) The electro-optical system manufactured by the method described in Example 1b) has good manufacturability, a wide operating temperature range, electro-optical parameters and their It is characterized by advantageous values for temperature dependence, low threshold voltage and high contrast.

Example 11 a) An electro-optical liquid crystal system containing a liquid crystal mixture consisting of the following compounds: 16.9% p-trans-4-propylcyclohexylbenzonitrile; 13.7% p-trans-4- Butylcyclohexylbenzonitrile; 22.5% p-trans-4-pentylcyclohexylbenzonitrile; 14.5% p-trans-4-heptylcyclohexylbenzonitrile; 5.6% 4- (trans-4-pentyl) Cyclohexyl) -4 '-(trans-4-propylcyclohexyl) biphenyl; 4.8% of 4-pentyl-4 "-cyanoterphenyl; 6.4% of trans-4-butylcyclohexylcarboxylic acid 4- (trans- 4-propylcyclohexyl) phenyl; 5.6% of 4- (trans-4-pentene) Cyclohexyl) -4'-cyanobiphenyl; 10.0% 1- [4- (trans-4- (trans -
4-propylcyclohexyl) cyclohexyl] phenyl] -2- (4-cyanophenyl) ethane.

B) The electro-optical systems produced by the method described in Example 1 b) have good manufacturability, a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, low threshold voltages and good High contrast.

Reference Example 27 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters: 14.4% p-trans-4-propylcyclohexylbenzonitrile; 2% p-trans-4-butylcyclohexylbenzonitrile; 20% p-trans-4-pentylcyclohexylbenzonitrile; 12% p-trans-4-heptylcyclohexylbenzonitrile; 5.6% 4- ( Trans-4-pentylcyclohexyl) -4 '-(trans-4-propylcyclohexyl) biphenyl; 4.8% of 4-pentyl-4 "-cyanoterphenyl; 6.4% of trans-4-butylcyclohexylcarboxylic acid 4- (trans-4-propylcyclohexyl) phenyl; 5.6 Of 4- (trans-4-pentylcyclohexyl) -4'-cyanobiphenyl; 20% of the 3- (4-isothiocyanatophenyl) -5-
Pentyl pyrimidine.

Clearing point TC = 83 ° C. Viscosity η = 28 mm ² / sec (20 ° C.) Optical anisotropy Δn = 0.18 (20 ° C., 589 nm) Dielectric anisotropy Δε = 14.6 (20 ° C. 1 kHz) b) The electro-optical system produced by the method described in Example 1 b) has good manufacturability, a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, low threshold voltages and good It is characterized by contrast.

Reference Example 28 a) Electro-optical liquid crystal system containing a liquid crystal mixture consisting of the following compounds: 16.2% p-trans-4-propylcyclohexylbenzonitrile; 12.6% p-trans-4- Butylcyclohexylbenzonitrile; 22.5% p-trans-4-pentylcyclohexylbenzonitrile; 13.5% p-trans-4-heptylcyclohexylbenzonitrile; 6.3% 4- (trans-4-pentyl) Cyclohexyl) -4 '-(trans-4-propylcyclohexyl) biphenyl; 5.4% of 4-pentyl-4 "-cyanoterphenyl; 7.2% of 4- (trans-butylcyclohexylcarboxylic acid 4- (trans- 4-propylcyclohexyl) phenyl; 6.3% of 4- (trans-4-pentene) Cyclohexyl) -4'-cyanobiphenyl; 10% 1- (trans-4-pentyl-4-isothiocyanatobenzene.

B) An electro-optical liquid crystal system is manufactured by the method described in Examples 1b), 1.1 to 1.3 and 2.

The electro-optical systems produced by this method are characterized by good manufacturability, wide operating temperature range, advantageous values for electro-optical parameters and their temperature dependence, low threshold voltage and high contrast.

Reference Example 29 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters: 14.4% p-trans-4-propylcyclohexylbenzonitrile; 2% p-trans-4-butylcyclohexylbenzonitrile; 20% p-trans-4-pentylcyclohexylbenzonitrile; 12% p-trans-4-heptylcyclohexylbenzonitrile; 5.6% 4- ( Trans-4-pentylcyclohexyl) -4 '-(trans-4-propylcyclohexyl) biphenyl; 4.8% of 4-pentyl-4 "-cyanoterphenyl; 6.4% of trans-4-butylcyclohexylcarboxylic acid 4- (trans-4-propylcyclohexyl) phenyl; 5.6 4- (trans-4-pentylcyclohexyl) -4'-cyanobiphenyl; 12% 1- (trans-4-propylcyclohexyl) -4-isothiocyanatobenzene; 8% 1- (trans-4-butyl) Cyclohexyl)-
4-isothiocyanatobenzene.

Clearing point TC = 80 ° C. Viscosity η = 24 mm ² / sec (20 ° C.) Optical anisotropy Δn = 0.15 (20 ° C., 589 nm) Dielectric anisotropy Δε = 11.8 (20 ° C., 1 kHz) b) An electro-optical liquid crystal system is manufactured by the method described in Examples 1b), 1.1 to 1.3 and 2.

The electro-optical systems produced by this method are characterized by good manufacturability, a wide operating temperature range, advantageous values for electro-optical parameters and their temperature dependence, low threshold voltages and high contrast.

Reference Example 30 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters: 14.4% p-trans-4-propylcyclohexylbenzonitrile; 2% p-trans-4-butylcyclohexylbenzonitrile; 20% p-trans-4-pentylcyclohexylbenzonitrile; 12% p-trans-4-heptylcyclohexylbenzonitrile; 5.6% 4- ( Trans-4-pentylcyclohexyl) -4 '-(trans-4-propylcyclohexyl) biphenyl; 4.8% of 4-pentyl-4 "-cyanoterphenyl; 6.4% of trans-4-butylcyclohexylcarboxylic acid 4- (trans-4-propylcyclohexyl) phenyl; 5.6 4- (trans-4-pentylcyclohexyl) -4′-cyanobiphenyl; 10% 4- (trans-4-propylcyclohexyl) -4′-difluoromethoxybiphenyl; 10% 4- (trans-4-pentyl) (Cyclohexyl) -4′-difluoromethoxybiphenyl.

Clearing point TC = 102 ° C. Viscosity η = 31 mm ² / sec (20 ° C.) Optical anisotropy Δn = 0.15 (20 ° C., 589 nm) Dielectric anisotropy Δε = 11.4 (20 ° C. 1 kHz) b) The electro-optical system produced by the method described in Example 1 b) has good manufacturability, a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, low threshold voltages and good It is characterized by contrast.

Reference Example 31 a) Electro-optical liquid crystal system containing a liquid crystal mixture consisting of the following compounds: 16.2% p-trans-4-propylcyclohexylbenzonitrile; 12.6% p-trans-4- Butylcyclohexylbenzonitrile; 22.5% p-trans-4-pentylcyclohexylbenzonitrile; 5.4% 4-pentyl-4 "-cyanoterphenyl; 7.2% trans-4-butylcyclohexylcarboxylic acid 4- (trans-4-propylcyclohexyl) phenyl; 6.3% of 4- (trans-4-pentylcyclohexyl) -4'-cyanobiphenyl; 10% of 4-pentyl-4 "-difluoromethoxyterphenyl; 5.5% p-trans-4-heptylcyclohexylbenzonitrile; 6.3% - (trans-4-pentylcyclohexyl) -4 '- (trans-4-propyl-cyclohexyl biphenyl.

B) The electro-optical system produced by the method described in Example 1 b) has good manufacturability, wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, low threshold voltage and high It is characterized by contrast.

Reference Example 32 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters: 14.4% p-trans-4-propylcyclohexylbenzonitrile; 2% p-trans-4-butylcyclohexylbenzonitrile; 20% p-trans-4-pentylcyclohexylbenzonitrile; 12% p-trans-4-heptylcyclohexylbenzonitrile; 5.6% 4- ( Trans-4-pentylcyclohexyl) -4 '-(trans-4-propylcyclohexyl) biphenyl; 4.8% of 4-pentyl-4 "-cyanoterphenyl; 6.4% of trans-4-butylcyclohexylcarboxylic acid 4- (trans-4-propylcyclohexyl) phenyl; 5.6 Of 4- (trans-4-pentylcyclohexyl) -4'-cyanobiphenyl; 20% 1- (trans-4-pentylcyclohexyl) -4-fluorobenzene.

Viscosity η = 20 mm ² / sec (20 ° C.) Optical anisotropy Δn = 0.12 (20 ° C., 589 nm) Dielectric anisotropy Δε = 10.2 (20 ° C., 1 kHz) b) Examples The electro-optical systems produced by the method described under 1b) are characterized by good manufacturability, a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, low threshold voltages and good contrast.

Reference Example 33 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters: 14.4% p-trans-4-propylcyclohexylbenzonitrile; 2% p-trans-4-butylcyclohexylbenzonitrile; 20% p-trans-4-pentylcyclohexylbenzonitrile; 12% p-trans-4-heptylcyclohexylbenzonitrile; 5.6% 4- ( Trans-4-pentylcyclohexyl) -4 '-(trans-4-propylcyclohexyl) biphenyl; 4.8% of 4-pentyl-4 "-cyanoterphenyl; 6.4% of trans-4-butylcyclohexylcarboxylic acid 4- (trans-4-propylcyclohexyl) phenyl; 5.6 Of 4- (trans-4-pentylcyclohexyl) -4'-cyanobiphenyl; 20% of the 2- (4- (3,4-difluorophenyl) phenyl) heptyl pyrimidine to 5.

Clearing point TC = 97 ° C. Viscosity η = 48 mm ² / sec (20 ° C.) Optical anisotropy Δn = 0.16 (20 ° C., 589 nm) Dielectric anisotropy Δε = 12.9 (20 ° C., 1 kHz) b) The electro-optical system produced by the method described in Example 1 b) has good manufacturability, a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, low threshold voltages and good It is characterized by contrast.

Reference Example 34 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters: 5% of 4- (trans-4-pentylcyclohexyl)
17.1% p-trans-4-propylcyclohexylbenzonitrile; 13.3% p-trans-4-butylcyclohexylbenzonitrile; 23.8% p-trans-4-. 14.3% of 4- (trans-4-heptylcyclohexyl) benzonitrile; 6.7% of 4- (trans-4-pentylcyclohexyl) -4'-cyanobiphenyl; 6.7% of pentylcyclohexylbenzonitrile; 4- (trans-4-pentylcyclohexyl) -4 '-(trans-4-propylcyclohexyl) biphenyl; 5.7% of 4-pentyl-4 "-cyanoterphenyl; 7.6% of trans-4-butyl 4- (trans-4-propylcyclohexyl) phenyl cyclohexylcarboxylate.

Clearing point TC = 95 ° C. Optical anisotropy Δn = 0.15 (20 ° C., 589 nm) Dielectric anisotropy Δε = 11.6 (20 ° C., 1 kHz) Flow viscosity η = 31 mm ² / sec ( B) The electro-optical systems produced by the method described in Example 1 b) are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters, and especially high UV stability.

Reference Example 35 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters: 20% of 1- (trans-4-pentylcyclohexyl) -4-chlorobenzene 14.4% p-trans-4-propylcyclohexylbenzonitrile; 11.2% p-trans-4-butylcyclohexylbenzonitrile; 20% p-trans-4-pentylcyclohexylbenzonitrile; 12% p-trans-4-heptylcyclohexylbenzonitrile; 5.6% of 4- (trans-4-pentylcyclohexyl) -4'-cyanobiphenyl; 5.6% of 4- (trans-4-pentylcyclohexyl) -4. '-(Trans-4-propylcyclohexyl) biphenyl; 4.8% - pentyl-4 "- cyano terphenyl; 6.4% of trans-4-butylcyclohexyl-carboxylic acid 4- (trans-4-propyl) phenyl.

Clearing point TC = 69 ° C. Optical anisotropy Δn = 0.13 (20 ° C., 589 nm) Dielectric anisotropy Δε = 10.8 (20 ° C., 1 kHz) Flow viscosity η = 21 mm ² / sec ( B) The electro-optical systems produced by the method described in Example 1 b) are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters, and especially high UV stability.

Reference Example 36 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters: 5.0% of 2-fluoro-4- (trans-4-pentylcyclohexyl) ) -3 ", 4"-difluoroterphenyl; 8.0% of 1- [4- (2-fluoro-4-propylphenyl) -phenyl] -2- (4-fluorophenyl)
Ethane; 11.0% 1- [4- (2-fluoro-4-pentylphenyl) -phenyl] -2- (4-fluorophenyl) ethane; 7.0% 1- {4- [4- ( Trans-4-propylcyclohexyl) -2-fluorophenyl] -phenyl {-2- (3,4-difluorophenyl) ethane; 7.0% of 1- {4- [4- (trans-4-pentylcyclohexyl)] -2-fluorophenyl] -phenyl} -2- (3,4-difluorophenyl) ethane; 2.0% of 1- {4- [4- (trans-4-propylcyclohexyl) -2-fluorophenyl]- Phenyl {-2- (3-fluorophenyl) ethane; 6.0% of 1- {4- [4- (trans-4-pentylcyclohexyl) -2-fluorophenyl] -phenyl} -2- (3 Fluorophenyl) ethane; 10.0% 4- (trans-4-ethyl-cyclohexyl) -3 ', 4'-difluoro-biphenyl; 10.0% 1- (4-pentylphenyl) -2- [4
-(3,4-difluorophenyl) -phenyl] ethane; 10.0% of 4- (trans-4-propylcyclohexyl) -3 ', 4'-difluorobiphenyl; 10.0% of 4- (trans-4 -Pentylcyclohexyl) -3 ', 4'-difluorobiphenyl; 7.0% of 4- (trans-4-ethylcyclohexyl) -3', 4 ', 5'-trifluorobiphenyl; 7.0% of 4- (Trans-4-pentylcyclohexyl) -3 ′, 4 ′, 5′-trifluorobiphenyl; clearing point TC = 97 ° C. optical anisotropy Δn = 0.1660 (20 ° C., 589 nm) ordinary refractive index n ₀ = 1.5115 (20 ° C., 589 nm) Dielectric anisotropy Δε = 7.6 (20 ° C., 1 kHz) b) The electro-optical system manufactured by the method described in Example 1b) has a wide operating temperature range, It is characterized by advantageous values for the optical parameters and especially high UV stability.

Reference Example 37 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters: 12.1% of trans-4- (trans-4-propylcyclohexyl) cyclohexyl 9.9% trans-4- (trans-4-pentylcyclohexyl) cyclohexylcarboxylate 3-fluoro-4-chlorophenylcarboxylate; 9.0% trans-4-propylcyclohexylcarboxylate 3-fluoro-4-chlorophenyl acid; 9.0% 3-fluoro-4-chlorophenyl trans-4-pentylcyclohexylcarboxylate; 10.0% trans-4- (trans-4-pentylcyclohexyl) cyclohexylcarboxylic acid 2-fluoro-4-pentyl Phenyl; 10.0% of 2-fluoro-4-pentylphenyl trans-4- (trans-4-propylcyclohexyl) cyclohexylcarboxylate; 10.0% of trans-4- (trans-4-propylcyclohexyl) cyclohexylcarboxylate 2-fluoro-4-pentylphenyl acid; 15.0% of 4- (trans-4-propylcyclohexyl) benzonitrile; 10.0% of 4- (trans-4-pentylcyclohexyl) benzonitrile; 5.0% 4- (trans-4-pentylcyclohexyl) -4 ′-(trans-4-propylcyclohexyl) biphenyl.

Viscosity η = 30.4 mm ² / sec (20 ° C.) Birefringence Δn = 0.11 (20 ° C., 589 nm) Clearing point N 114.9 I b) Produced by the method described in Example 1b). Electro-optical systems are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters, and especially high UV stability.

Reference Example 38 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters: 12.1% of trans-4- (trans-4-propylcyclohexyl) cyclohexyl 9.9% trans-4- (trans-4-pentylcyclohexyl) cyclohexylcarboxylate 3-fluoro-4-chlorophenylcarboxylate; 9.0% trans-4-propylcyclohexylcarboxylate 3-fluoro-4-chlorophenyl acid; 9.0% trans-4-pentylcyclohexylcarboxylic acid 3-fluoro-4-chlorophenyl acid; 8.0% trans-4- (trans-4-pentylcyclohexyl) cyclohexylcarboxylic acid 2-fluoro-4-pentylph 7.0% of 2-fluoro-4-pentylphenyl trans-4- (trans-4-propylcyclohexyl) cyclohexylcarboxylate; 7.0% of trans-4- (trans-4-propylcyclohexyl) cyclohexylcarboxylate 2-fluoro-4-propylphenyl acid; 15.0% 4- (trans-4-propylcyclohexyl) benzonitrile; 13.0% 4- (trans-4-pentylcyclohexyl) benzonitrile; 2.0% 4- (trans-4-pentylcyclohexyl) -4 '-(trans-4-propylcyclohexyl) biphenyl; 8.0% of 4-pentylphenyl trans-4-propylcyclohexylcarboxylate.

Viscosity η = 25.9 mm ² / sec (20 ° C.) Birefringence Δn = 0.10 (20 ° C., 589 nm) Clearing point N 94.2 I b) Produced by the method described in Example 1b). Electro-optical systems are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters, and especially high UV stability.

Reference Example 39 a) An electro-optical liquid crystal system containing a liquid crystal mixture consisting of the following compounds and having the following physical parameters: 14.4% p-trans-4-propylcyclohexylbenzonitrile; 2% p-trans-4-butylcyclohexylbenzonitrile; 20% p-trans-4-pentylcyclohexylbenzonitrile; 12% p-trans-4-heptylcyclohexylbenzonitrile; 5.6% 4- ( Trans-4-pentylcyclohexyl) -4 '-(trans-4-propylcyclohexyl) biphenyl; 4.8% of 4-pentyl-4 "-cyanoterphenyl; 6.4% of trans-4-butylcyclohexylcarboxylic acid 4- (trans-4-propylcyclohexyl) phenyl; 5.6 4- (trans-4-pentylcyclohexyl) -4′-cyanobiphenyl; 6% 4-propylphenyl-4-heptyl benzoate; 7% 4-pentylphenyl-4-heptyl benzoate; 7.0% 4-heptylphenyl-4-heptyl benzoate.

Clearing point TC = 77 ° C. Viscosity η = 34 mm ² / sec (20 ° C.) Optical anisotropy Δn = 0.14 (20 ° C., 589 nm) b) Electricity produced by the method described in Example 1b) The optical system is characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and in particular a low threshold voltage.

Reference Example 40 a) Electro-optical liquid crystal system containing a liquid crystal mixture consisting of the following compounds: 12% of 4- (trans-4-pentylcyclohexyl) benzonitrile; 20% of 4-propyl-4'-cyano Biphenyl; 13% 4-pentyl-4'-cyanobiphenyl; 20% 4- (trans-4-pentylcyclohexyl) -4'-cyanobiphenyl; 15% 4-propyl-3'-fluoro-4 "-. Cyanoterphenyl; 20% 4-pentoxy-4'-fluorotolan.

B) The electro-optical system produced by the method described in Example 1 b) has good manufacturability, a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, low threshold voltage and high It is characterized by contrast.

Reference Example 41 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters: 18% of 4-cyano-4 '-(trans-4-pentylcyclohexyl) Biphenyl; 35% 4-cyano-4'-hexylbiphenyl; 22% 4-cyano-4'-pentylbiphenyl; 9% 4-cyano-4 "-pentylterphenyl; 5% 4-cyano-4 '-Yl-biphenyl-4-heptyl-4'-yl-biphenylcarboxylate; 5% of 4-cyano-4'-nonoxybiphenyl; 6% of 1- (trans-4-propylcyclohexyl)
-2- (4-pentyl-2-fluoro-4'-yl-biphenyl) ethane.

Clearing point TC = 100 ° C. Viscosity η = 55 mm ² / sec (20 ° C.) Dielectric anisotropy Δε = 14.1 (20 ° C., 589 nm) Optical anisotropy Δn = 0.24 (20 ° C., 1 kHz) b) The electro-optical system produced by the method described in Example 1 b) has a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and low threshold voltages, good manufacturability and high It is characterized by contrast.

Reference Example 42 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters: 25% of 2- (4-cyanophenyl) -5-propylpyridine; 25 % 2- (4-cyanophenyl) -5-butylpyridine; 25% 2- (4-cyanophenyl) -5-pentylpyridine; 25% 2- (4-cyanophenyl) -5- (pentylphenyl) ) Pyridine.

Clearing point TC = 85 ° C. Viscosity η = 70 mm ² / sec (20 ° C.) Optical anisotropy Δn = 0.269 (20 ° C., 589 nm) Dielectric anisotropy Δε = 24.1 (20 ° C. 1 kHz) b) The electro-optical liquid-crystal systems produced by the method described in example 1 b) have good manufacturability, a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, low threshold voltages and It features high contrast.

Example 12 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters: 17.5% of 2- (4-cyanophenyl) -5-propylpyridine 17.5% 2- (4-cyanophenyl) -5-butylpyridine; 17.5% 2- (4-cyanophenyl) -5-pentylpyridine; 17.5% 2- (4-cyano) Phenyl) -5- (4-
Pentylphenyl) pyridine; 15.0% 1- [4- (4-propylphenyl) phenyl-2- (3-fluoro-4-cyanophenyl) ethane; 15.0% 1- [4- (4- (Pentylphenyl) phenyl-2- (3-fluoro-4-cyanophenyl) ethane.

Clearing point TC = 94 ° C. Optical anisotropy Δn = 0.272 (20 ° C., 589 nm) Dielectric anisotropy Δε = 25.6 (20 ° C., 1 kHz) b) Described in Example 1b) The electro-optical liquid crystal systems produced by the method are characterized by good manufacturability, a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, low threshold voltages and high contrast.

Example 13 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters: 22.5% of 2- (4-cyanophenyl) -5-propylpyridine 22.5% 2- (4-cyanophenyl) -5-butylpyridine; 22.5% 2- (4-cyanophenyl) -5-pentylpyridine; 22.5% 2- (4-cyanophenyl); Phenyl) -5- (4-
Pentylphenyl) pyridine; 10.0% 1- (4-propylphenyl) phenyl-
2- [4- (3-Fluoro-4-cyanophenyl) phenyl] ethane.

Clearing point TC = 82 ° C. Viscosity η = 74 mm ² / sec (20 ° C.) Optical anisotropy Δn = 0.260 (20 ° C., 589 nm) Dielectric anisotropy Δε = 25 (20 ° C., 1 kHz) b) The electro-optical liquid-crystal systems produced by the method described in Example 1 b) have good manufacturability, a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, low threshold voltages and high contrast. It is characterized by.

Reference Example 43 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical properties: 22.5% of 2- (4-cyanophenyl) -5-propylpyridine 22.5% 2- (4-cyanophenyl) -5-butylpyridine; 22.5% 2- (4-cyanophenyl) -5-pentylpyridine; 22.5% 2- (4-cyanophenyl); Phenyl) -5- (4-
Pentylphenyl) pyridine; 10.0% of 4-pentyl-3 ", 5" -difluoro-
4 "-cyanoterphenyl.

Clearing point TC = 84 ° C. Viscosity η = 75 mm ² / sec (20 ° C.) Optical anisotropy Δn = 0.266 (20 ° C., 589 nm) Dielectric anisotropy Δε = 26 (20 ° C., 1 kHz) b) The electro-optical liquid-crystal systems produced by the method described in Example 1 b) have good manufacturability, a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, low threshold voltages and high contrast. It is characterized by.

Reference Example 44 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical properties: 20.0% of 2- (4-cyanophenyl) -5-propylpyridine 20.0% 2- (4-cyanophenyl) -5-butylpyridine; 20.0% 2- (4-cyanophenyl) -5-pentylpyridine; 20.0% 2- (4-cyanophenyl) Phenyl) -5- (4-
Pentylphenyl) pyridine; 10.0% of 2- (3-fluoro-4-cyanophenyl) -5-propylpyrimidine; 10.0% of 2- (3-fluoro-4-cyanophenyl) -5-pentylpyrimidine .

Clearing point TC = 71 ° C. Viscosity η = 68 mm ² / sec (20 ° C.) Optical anisotropy Δn = 0.253 (20 ° C., 589 nm) Dielectric anisotropy Δε = 29.5 (20 ° C. 1 kHz) b) The electro-optical liquid-crystal systems produced by the method described in example 1 b) have good manufacturability, a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, low threshold voltages and It features high contrast.

Example 14 a) An electro-optical liquid crystal system containing a liquid crystal mixture consisting of the following compounds and having the following physical properties: 15.0% p-trans-4-propylcyclohexylbenzonitrile; 0% p-trans-4-butylcyclohexylbenzonitrile; 20.0% p-trans-4-pentylcyclohexylbenzonitrile; 12.0% p-trans-4-heptylcyclohexylbenzonitrile; 6.0% 4- (trans-4-pentylcyclohexyl-4'-cyanobiphenyl); 6.0% of 4- (trans-4-pentylcyclohexyl-4 '-(trans-4-propylcyclohexyl)
Biphenyl; 5.0% of 4-pentyl-4 "-cyanoterphenyl; 6.0% of 4- (trans-4-propylcyclohexyl) phenyl trans-4-butylcyclohexylcarboxylate; 20.0% of 1- [Trans-4- (trans-4-propylcyclohexyl) cyclohexyl] -2- (3-
Fluoro-4-cyanophenyl) ethane.

Clearing point TC = 98 ° C. Viscosity η = 39 mm ² / sec (20 ° C.) Optical anisotropy Δn = 0.139 (20 ° C., 589 nm) Dielectric anisotropy Δε = 14 (20 ° C., 1 kHz) b) The electro-optical liquid crystal system produced by the method described in Example 1b) has good manufacturability, a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, good contrast, and good contrast. It is characterized by low angle dependence.

Example 15 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical properties: 15.0% p-trans-4-propylcyclohexylbenzonitrile; 0% p-trans-4-butylcyclohexylbenzonitrile; 20.0% p-trans-4-pentylcyclohexylbenzonitrile; 12.0% p-trans-4-heptylcyclohexylbenzonitrile; 6.0% 4- (trans-4-pentylcyclohexyl-4'-cyanobiphenyl); 6.0% of 4- (trans-4-pentylcyclohexyl-4 '-(trans-4-propylcyclohexyl)
Biphenyl; 5.0% of 4-pentyl-4 "-cyanoterphenyl; 6.0% of 4- (trans-4-propylcyclohexyl) phenyl trans-4-butylcyclohexylcarboxylate; 20.0% of 1- (Trans-4-pentylcyclohexyl) -2- (3-fluoro-4-phenyl) ethane.

Clearing point TC = 76 ° C. Viscosity η = 30 mm ² / sec (20 ° C.) Optical anisotropy Δn = 0.130 (20 ° C., 589 nm) Dielectric anisotropy Δε = 13 (20 ° C., 1 kHz) b) The electro-optical liquid crystal system produced by the method described in Example 1b) has good manufacturability, a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, good contrast, and good contrast. It is characterized by small angle dependence.

Reference Example 45 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical properties: 15.0% p-trans-4-propylcyclohexylbenzonitrile; 0% p-trans-4-butylcyclohexylbenzonitrile; 20.0% p-trans-4-pentylcyclohexylbenzonitrile; 12.0% p-trans-4-heptylcyclohexylbenzonitrile; 6.0% 4- (trans-4-pentylcyclohexyl-4'-cyanobiphenyl); 6.0% of 4- (trans-4-pentylcyclohexyl-4 '-(trans-4-propylcyclohexyl)
Biphenyl; 5.0% of 4-pentyl-4 "-cyanoterphenyl; 6.0% of 4- (trans-4-propylcyclohexyl) phenyl trans-4-butylcyclohexylcarboxylate; 20.0% of 4- Pentyl-4'-chlorobiphenyl.

Clearing point TC = 74 ° C. Viscosity η = 27 mm ² / sec (20 ° C.) Optical anisotropy Δn = 0.150 (20 ° C., 589 nm) Dielectric anisotropy Δε = 11 (20 ° C., 1 kHz) b) The electro-optical liquid crystal system produced by the method described in Example 1b) has good manufacturability, a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, good contrast, and good contrast. It is characterized by small angle dependence.

Reference Example 46 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical properties: 16.0% p-trans-4-propylcyclohexylbenzonitrile; 0% p-trans-4-butylcyclohexylbenzonitrile; 23.0% p-trans-4-pentylcyclohexylbenzonitrile; 13.0% p-trans-4-heptylcyclohexylbenzonitrile; 6.0% 4- (trans-4-pentylcyclohexyl-4′-cyanobiphenyl); 6.0% of 4- (trans-4-pentylcyclohexyl) -4 ′-(trans-4-propylcyclohexyl) biphenyl; 6.0% 4-pentyl-4 "-cyanoterphenyl; 7.0% of trans-4-butylcyclohexane 4- (trans-4-propylcyclohexyl) phenyl silyl carboxylate; 5.0% of 4- (trans-4-propylcyclohexyl) -4'-methoxytran; 5.0% of 4- (trans-4-propylcyclohexyl) ) -4'-Ethoxytran.

Clearing point TC = 106 ° C. Viscosity η = 30 mm ² / sec (20 ° C.) Optical anisotropy Δn = 0.163 (20 ° C., 589 nm) Dielectric anisotropy Δε = 10.5 (20 ° C. 1 kHz) b) The electro-optical liquid crystal system produced by the method described in Example 1 b) has good manufacturability, a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, good contrast, and It is characterized in that the angle dependence of contrast is small.

Reference Example 47 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical properties: 15.0% p-trans-4-propylcyclohexylbenzonitrile; 0% p-trans-4-butylcyclohexylbenzonitrile; 20.0% p-trans-4-pentylcyclohexylbenzonitrile; 12.0% p-trans-4-heptylcyclohexylbenzonitrile; 6.0% 4- (trans-4-pentylcyclohexyl-4'-cyanobiphenyl); 6.0% of 4- (trans-4-pentylcyclohexyl-4 '-(trans-4-propylcyclohexyl)
Biphenyl; 5.0% of 4-pentyl-4 "-cyanoterphenyl; 6.0% of 4- (trans-4-propylcyclohexyl) phenyl trans-4-butylcyclohexylcarboxylate; 20.0% of 4- (Trans-4-propylcyclohexyl) -3 ′, 4 ′, 5′-trifluorobiphenyl.

Clearing point TC = 82 ° C. Viscosity η = 32 mm ² / sec (20 ° C.) Optical anisotropy Δn = 0.138 (20 ° C., 589 nm) Dielectric anisotropy Δε = 13.5 (20 ° C. 1 kHz) b) The electro-optical liquid crystal system produced by the method described in Example 1 b) has good manufacturability, a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, good contrast, and It is characterized in that the angle dependence of contrast is small.

Example 15 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical properties: 15.0% p-trans-4-propylcyclohexylbenzonitrile; 0% p-trans-4-butylcyclohexylbenzonitrile; 20.0% p-trans-4-pentylcyclohexylbenzonitrile; 12.0% p-trans-4-heptylcyclohexylbenzonitrile; 6.0% 4- (trans-4-pentylcyclohexyl) -4'-cyanobiphenyl; 6.0% of 4- (trans-4-pentylcyclohexyl) -4 '-(trans-4-propylcyclohexyl) biphenyl; 5.0 % 4-pentyl-4 "-cyanoterphenyl; 6.0% trans-4-butylcyclo 4-cyclohexyl-carboxylic acid (trans-4-propyl) phenyl; 10.0% 1- (trans-4- (trans-4-propyl-cyclohexyl) cyclohexyl) -2- (4-
Cyanophenyl) ethane; 10.0% of 1- (trans-4- (trans-4-pentylcyclohexyl) cyclohexyl) -2- (4-
Cyanophenyl) ethane.

Clearing point TC = 111 ° C. Viscosity η = 36 mm ² / sec (20 ° C.) Dielectric anisotropy Δε = 11.8 (20 ° C., 1 kHz) b) Produced by the method described in Example 1b) Electro-optical liquid crystal systems are characterized by good manufacturability, a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, good contrast, and low angular dependence of the contrast.

Reference Example 48 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical properties: 15.0% p-trans-4-propylcyclohexylbenzonitrile; 0% p-trans-4-butylcyclohexylbenzonitrile; 20.0% p-trans-4-pentylcyclohexylbenzonitrile; 12.0% p-trans-4-heptylcyclohexylbenzonitrile; 6.0% 4- (trans-4-pentylcyclohexyl-4′-cyanobiphenyl); 6.0% of 4- (trans-4-pentylcyclohexyl) -4 ′-(trans-4-propylcyclohexyl) biphenyl; 5.0% 4-pentyl-4 "-cyanoterphenyl; 6.0% of trans-4-butylcyclohexane Shirukarubon acid 4- (trans-4-propyl) phenyl; 10.0% 1- (4-propylphenyl) -2- [4
-(2-fluoro-4-pentylphenyl) phenyl]
Ethane; 10.0% of 1- (4-pentylphenyl) -2- [4
-(2-fluoro-4-propylphenyl) phenyl]
Ethane.

Clearing point TC = 85 ° C. Viscosity η = 29 mm ² / sec (20 ° C.) Optical anisotropy Δn = 0.146 (20 ° C., 589 nm) b) Produced by the method described in Example 1b). Electro-optical liquid crystal systems are characterized by good manufacturability, a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, good contrast, and low angular dependence of the contrast.

Reference Example 49 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical properties: 34.65% of 4-pentyl-4'-cyanobiphenyl; 13.5 % Of 4-propoxy-4'-cyanobiphenyl; 10.35% of 4-pentoxy-4'-cyanobiphenyl; 13.5% of 4-octoxy-4'-cyanobiphenyl; 10.0% of 4- ( Trans-4-pentylcyclohexyl) -4'-cyanobiphenyl; 9.0% of 4- [2- (p-propylphenyl) ethyl] -4'-cyanobiphenyl; and 9.0% of 4-
[2- (p-pentylphenyl) ethyl] -4′-cyanobiphenyl.

NI 84 ° C. Δn 0.247 (20 ° C., 589 nm) b) The electro-optical liquid crystal system manufactured by the method described in Example 1b) has good manufacturability, a wide operating temperature range, and electro-optics. It is characterized by advantageous values for the parameters and their temperature dependence, good contrast and low angular dependence of the contrast.

Reference Example 50 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters: 20% of 4-pentyl-4'-cyanobiphenyl; 23% of 2- (4-cyanophenyl) -5-pentylpyridine; 17% of 4-propoxy-4'-cyanobiphenyl; 13% of 4-pentoxy-4'-cyanobiphenyl; 17% of 4-octoxy-4'-cyanobiphenyl 10.0% of 4-pentyl-4 "-cyanoterphenyl.

Clearing point TC = 70.4 ° C. Viscosity η = 61 mm ² / sec (20 ° C.) Threshold voltage V [90.0.20] = 1.31V The threshold voltage was as shown in Reference Example 5a. Measure.

B) An electro-optical liquid crystal system is manufactured by the method described in Example 1 b).

Reference Example 51 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters: 12% of 2- (4-cyanophenyl) -5-propylpyridine; % 2- (4-cyanophenyl) -5-pentylpyridine; 18% 4-pentyl-4'-cyanobiphenyl; 9% 4-propoxy-4'-cyanobiphenyl; 9% 4-pentyl-4 "-Cyanobiphenyl; 22% of 4-propyl-2'-fluoro-4"-cyanoterphenyl; 15% of 4- (trans-4-pentylcyclohexyl) -4'-cyanobiphenyl.

Clearing point TC = 114 ° C. Viscosity η = 86.6 mm ² / sec (20 ° C.) Threshold voltage V [90.0.20] = 1.69V The threshold voltage was as shown in Reference Example 5a. Measure.

B) An electro-optical liquid crystal system is manufactured by the method described in Example 1 b).

Reference Example 52 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters: 12% of 2- (4-cyanophenyl) -5-propylpyridine; % 2- (4-cyanophenyl) -5-pentylpyridine; 5% 4-cyanobiphenyl; 8.5% 4-ethyl-4'-cyanobiphenyl; 8.5% 4-propyl-4 '. 20% 4-pentyl-4'-cyanobiphenyl; 17% 4-propyl-2'-fluoro-4 "-cyanotelphenyl; 9% 4-pentyl-4" -cyanotelphenyl.

Clearing point TC = 69.6 ° C. Viscosity η = 51 mm ² / sec (20 ° C.) Threshold voltage V [90.0.20] = 1.29V The threshold voltage was as shown in Reference Example 5a. Measure.

B) An electro-optical liquid crystal system is manufactured by the method described in Example 1 b).

Reference Example 53 a) A liquid crystal mixture consisting of the following compounds has the following physical properties: 14.0% of 4-ethyl-4'-cyanobiphenyl; 15.0% of 4-butyl 41.9% 4-hexyl-4'-cyanobiphenyl; 2.5% 4-methoxy-4'-cyanobiphenyl; 12.0% 4-propoxy-4'-cyano Biphenyl; 7.6% of 4-pentyl-4 "-cyanoterphenyl; 3.0% of 4- (4-pentylphenyl) benzoic acid 4-
(4-cyanophenyl) phenyl; 4.0% of 4- (4-heptylphenyl) benzoic acid 4-
(3-cyanophenyl) phenyl.

Birefringence Δn = 0.232 (20 ° C., 589 nm) Ordinary refractive index n0 = 1.766 (20 ° C., 589 nm) Dielectric anisotropy Δε = 15.8 (20 ° C., 1 kHz) Threshold Voltage V [10.0.20] = 1.23V Clearing point TC = 64 ° C. The threshold voltage has a cell interval of 7 μm, and a TN cell placed between orthogonal polarizers (twist angle ψ = π / 4) Was measured.

B) The electro-optical systems produced by the method described in Example 1 b) are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and especially low threshold voltages.

Example 17 a) A liquid crystal mixture consisting of the following compounds has the following physical properties: 34.0% of 4-pentyl-4'-cyanobiphenyl; 10.0% of 4-propoxy 13.0% of 4-ethyl-4'-cyanobiphenyl; 10.0% of 4-pentoxy-4'-cyanobiphenyl; 13.0% of 4- (4-pentylphenyl) -4'-cyanophenyl; 10.0% of 4-octoxy-4'-cyanobiphenyl; 10.0% of 1- (trans-4- (trans-4-propylcyclohexyl) cyclohexyl-4- (4-cyano Phenyl) phenyl) ethane.

Birefringence Δn = 0.243 (20 ° C., 589 nm) Ordinary refractive index n0 = 1.765 (20 ° C., 589 nm) Clearing point TC = 91 ° b) Production by the method described in Example 1b) The described electro-optical system is characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and a particularly low threshold voltage.

Example 18 a) A liquid crystal mixture consisting of the following compounds has the following physical properties: 20.0% of 1- {4- [2-fluoro-4- (trans-4-pentyl) Cyclohexyl) phenyl] phenyl} -2- (4-fluorophenyl) ethane; 10.0% of 1- {4- [2-fluoro-4- (trans-4-pentylcyclohexyl) phenyl] phenyl} -2- ( 4-fluorophenyl) ethane; 30.0% of 1- {4- [2-fluoro-4-pentylphenyl) phenyl] -2- (4-chlorophenyl) ethane; 30.0% of 1- [4- ( 2-fluoro-4-pentylphenyl) phenyl] -2- (4-chlorophenyl) ethane; 10.0% of 1- [4- (trans-4-propylcyclohexyl) phenyl] -2- (4 -Fluorophenyl) ethane; Clearing point TC = 104 ° C. Optical anisotropy Δn = 0.189 (20 ° C., 589 nm) b) Electro-optical liquid crystal system produced by the method described in Example 1b) is a good production , Wide operating temperature range, advantageous values for the electro-optic parameters and their temperature dependence, good contrast, low angular dependence of the contrast, and especially high UV stability.

Reference Example 54 a) A liquid crystal mixture consisting of the following compounds has the following physical properties: 17.5% of 1- {4- [2-fluoro-4- (trans-4-pentyl) Cyclohexyl) phenyl] phenyl {-2- (4-fluorophenyl) ethane; 8.5% of 1- {4- [2-fluoro-4- (trans-4-pentylcyclohexyl) phenyl] phenyl}
-2- (4-chlorophenyl) ethane; 25.5% of 1- [4- (2-fluoro-4-pentylphenyl) phenyl] -2- (4-fluorophenyl)
Ethane; 25.5% 1- [4- (2-fluoro-4-pentylphenyl) phenyl] -2- (4-chlorophenyl) ethane; 8.5% 1- [4- (trans-4-propyl) Cyclohexyl) phenyl] -2- (4-fluorophenyl)
Ethane; 8.5% of 1- [4- (trans-4-pentylcyclohexyl) phenyl] -2- (4-fluorophenyl)
Ethane; 8.5% of 1- [4- (trans-4-propylcyclohexyl) phenyl] -2- (4-chlorophenyl) ethane.

Clearing point TC = 98 ° C. Optical isomer Δn = 0.176 (20 ° C., 589 nm) Dielectric anisotropy Δε = 5.0 (20 ° C., 1 kHz) b) By the method described in Example 1b) The electro-optical liquid crystal systems produced have good manufacturability, a wide operating temperature range, advantageous values for electro-optical parameters and their temperature dependence, good contrast, low contrast angle dependence, and especially high UV stability Characteristic.

Reference Example 55 a) A liquid crystal mixture consisting of the following compounds has the following physical properties: 17% of 1- {4- [2-fluoro-4- (trans-
4-pentylcyclohexyl) phenyl] phenyl}-
2- (4-fluorophenyl) ethane; 8.5% of 1- {4- [2-fluoro-4- (trans-4-pentylcyclohexyl) phenyl] phenyl}
-2- (4-chlorophenyl) ethane; 25.5% of 1- [4- (2-fluoro-4-pentylphenyl) phenyl] -2- (4-fluorophenyl)
Ethane; 25.5% 1- [4- (2-fluoro-4-pentylphenyl) phenyl] -2- (4-chlorophenyl) ethane; 8.5% 1- [4- (trans-4-propyl) Cyclohexyl) phenyl] -2- (4-fluorophenyl)
Ethane; 7.8% 1- (trans-4-pentylcyclohexyl) -1-chlorobenzene; 7.2% 4- (trans-4-heptylcyclohexyl) -1-chlorobenzene.

Clearing point TC = 87 ° C. Optical isomer Δn = 0.171 (20 ° C., 589 nm) b) The electro-optical liquid crystal system produced by the method described in Example 1b) has good productivity and wide operating temperature. It is characterized by advantageous values for the range, the electro-optical parameters and their temperature dependence, good contrast, low angle dependence of the contrast, and especially high UV stability.

Reference Example 56 a) A liquid crystal mixture consisting of the following compounds has the following physical properties: 10% of 1- {4- [2-fluoro-4- (trans-
4-pentylcyclohexyl) phenyl] phenyl}-
2- (4-fluorophenyl) ethane; 10% of 1- {4- [2-fluoro-4- (trans-
4-pentylcyclohexyl) phenyl] phenyl}-
2- (4-chlorophenyl) ethane; 20% 1- [4- (2-fluoro-4-pentylphenyl) phenyl] -2- (4-fluorophenyl) ethane; 10% 1- [4- (2 -Fluoro-4-pentylphenyl) phenyl] -2- (4-chlorophenyl) ethane; 10% of 4- (trans-4-pentylcyclohexyl) -1-chlorobenzene; 10% of 4- (trans-4-pentylcyclohexyl). ) -1-Chlorobenzene; 15% 4-propyl-2'-fluoro-4 "-ethylterphenyl; 15% 4-ethyl-2'-fluoro-4" -propylterphenyl.

Clearing point TC = 75 ° C. Optical anisotropy Δn = 0.142 (20 ° C., 589 nm) b) The electro-optical liquid crystal system produced by the method described in Example 1b) has good manufacturability and a wide range. It is characterized by advantageous values for the operating temperature range, the electro-optical parameters and their temperature dependence, good contrast, low angle dependence of the contrast, and especially high UV stability.

Reference Example 57 a) A liquid crystal mixture consisting of the following compounds has the following physical properties: 16.9% of 1- {4- [2-fluoro-4- (trans-4-pentyl) Cyclohexyl) phenyl] phenyl {-2- (4-fluorophenyl) ethane; 8.5% of 1- {4- [2-fluoro-4- (trans-4-pentylcyclohexyl) phenyl] phenyl}
-2- (4-chlorophenyl) ethane; 25.3% of 1- [4- (2-fluoro-4-pentylphenyl) phenyl] -2- (4-fluorophenyl)
Ethane; 25.3% 1- [4- (2-fluoro-4-pentylphenyl) phenyl] -2- (4-chlorophenyl) ethane; 8.5% 1- [4- (trans-4-propyl) Cyclohexyl) phenyl] -2- (4-fluorophenyl)
Ethane; 15.5% of 1- [trans-4- (trans-4-propylcyclohexyl) cyclohexyl] -2- (4-
Chlorophenyl) ethane.

Clearing point TC = 112 ° C. Optical anisotropy Δn = 0.178 (20 ° C., 589 nm) b) The electro-optical liquid crystal system produced by the method described in Example 1b) has good manufacturability and a wide range. It is distinguished by advantageous values for the operating temperature range, the electro-optical parameters and their temperature dependence, good contrast, low angle dependence of the contrast, and especially high UV stability.

Reference Example 58 a) A liquid crystal mixture consisting of the following compounds has the following physical properties: 17% of 1- {4- [2-fluoro-4- (trans-
4-pentylcyclohexyl) phenyl] phenyl}-
2- (4-fluorophenyl) ethane; 8.5% of 1- {4- [2-fluoro-4- (trans-4-pentylcyclohexyl) phenyl] phenyl}
-2- (4-chlorophenyl) ethane; 25.5% of 1- [4- (2-fluoro-4-pentylphenyl) phenyl] -2- (4-fluorophenyl)
Ethane; 25.5% 1- [4- (2-fluoro-4-pentylphenyl) phenyl] -2- (4-chlorophenyl) ethane; 8.5% 1- [4- (trans-4-propyl) Cyclohexyl) phenyl) phenyl] -2- (4-fluorophenyl) ethane; 7.6% of 4- (trans-4-pentylcyclohexyl) -1-fluorobenzene; 7.4% of 4- (trans-4- Hexylcyclohexyl) -1-fluorobenzene; clearing point TC = 80 ° C. optical anisotropy Δn = 0.172 (20 ° C., 589 nm) b) The electro-optical liquid crystal system produced by the method described in Example 1b) Good manufacturability, wide operating temperature range, favorable values for electro-optic parameters and their temperature dependence, good contrast, low contrast angle dependence It is distinguished by its high stability and particularly high UV stability.

Reference Example 59 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters: 14.4% p-trans-4-propylcyclohexylbenzonitrile; 2% p-trans-4-butylcyclohexylbenzonitrile; 20% p-trans-4-pentylcyclohexylbenzonitrile; 12% p-trans-4-heptylcyclohexylbenzonitrile; 5.6% 4- ( Trans-4-pentylcyclohexyl) cyclohexylcarboxylate 4- (trans-4-propylcyclohexyl) biphenyl; 4.8% of 4-pentyl-4 "-cyanoterphenyl; 6.4% of trans-4-butylcyclohexylcarboxylate Acid 4- (trans-4-propylcyclohexyl) ) Phenyl; 5.6% 4- (trans-4-pentylcyclohexyl) -4'-cyanobiphenyl; 6% 4-propylphenyl 4-heptylbenzoate 7% 4-pentylphenyl 4-heptylbenzoate 7 % 4-heptylphenyl 4-heptylbenzoate.

Clearing point TC = 77.5 ° C. Viscosity η = 34 mm ² / sec (20 ° C.) Optical anisotropy Δn = 0.14 (20 ° C., 589 nm) b) Manufactured by the method described in Example 1b) The resulting electro-optical system is characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and in particular a low threshold voltage.

Reference Example 60 a) Electro-optical liquid crystal system containing a liquid crystal mixture consisting of the following compounds: 20% of 1- (trans-4- (trans-4-propylcyclohexyl) -2- (3-fluoro-4) 14.4% p-trans-4-propylcyclohexylbenzonitrile; 11.2% p-trans-4-butylcyclohexylbenzonitrile; 20% p-trans-4-pentylcyclohexylbenzonitrile 4.8% p-trans-4-heptylcyclohexylbenzonitrile; 5.6% 4- (trans-4-propylcyclohexyl) phenyl trans-4- (trans-4-pentylcyclohexyl) cyclohexylcarboxylate; 4.8% % 4-pentyl-4 "-cyanoterphenyl; 6.4% 4- (trans-4-propylcyclohexyl) phenyl lance-4-butylcyclohexylcarboxylate; 4- (trans-4-pentylcyclohexyl) -4 ′
-Cyanobiphenyl.

B) The electro-optical systems produced by the method described in Example 1 b) are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and especially low threshold voltages.

Reference Example 61 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical parameters: 14.5% p-trans-4-propylcyclohexylbenzonitrile; 2% p-trans-4-butylcyclohexylbenzonitrile; 20% p-trans-4-pentylcyclohexylbenzonitrile; 12% p-trans-4-heptylcyclohexylbenzonitrile; 5.6% trans-4. 4- (trans-4-propylcyclohexyl) phenyl 4- (trans-4-pentylcyclohexyl) cyclohexylcarboxylate; 6.4% of 4- (trans-4-propylcyclohexyl) phenyl trans-4-butylcyclohexylcarboxylate; 0.6% of 4- (trans-4 Pentyl) -4'-cyanobiphenyl; 4.8% 4-pentyl-4 "- cyano terphenyl; 20% of the 2- (4-cyanophenyl) -5-pentyl pyrimidine.

Clearing point TC = 82.5 ° C. Viscosity η = 34 mm ² / sec (20 ° C.) Optical anisotropy Δn = 0.16 (20 ° C., 589 nm) Dielectric anisotropy Δε = 16.1 (20 B) The electro-optical systems produced by the method described in Example 1 b) are characterized by a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and especially low threshold voltages. .

Reference Example 62 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical properties: 10.0% of 2- (4-cyanophenyl) -5-propyltolu- 15.0% 2- (4-cyanophenyl) -5-butyltolu-1,3-dioxane; 15.0% 2- (4-cyanophenyl) -5-pentyltolu-1, 3-dioxane; 20.0% of 4- (trans-4-propylcyclohexyl) benzonitrile; 15.0% of 4- (trans-4-pentylcyclohexyl) benzonitrile; 10.0% of 4- (trans- 4-heptylcyclohexyl) benzonitrile; 5.0% trans-4- (trans-4-propylcyclohexyl) cyclohexylcarboxylic acid 4- (tran 5.0% trans-4- (trans-4-pentylcyclohexyl) cyclohexyl carboxylic acid 5.0% trans-4- (trans-4-pentylcyclohexyl) phenyl; 5.0% trans-4- (trans-4-pentylcyclohexyl) phenyl; Trans-4-pentylcyclohexyl) cyclohexylcarboxylate 4- (trans-4-propylcyclohexyl) phenyl.

Clearing point TC = 76 ° C. Viscosity η = 34 mm ² / sec (20 ° C.) Optical anisotropy Δn = 0.131 (20 ° C., 589 nm) Dielectric anisotropy Δε = 17 (1 kHz, 20 ° C.) b) The electro-optical liquid-crystal systems produced by the method described in Example 1b) have good manufacturability, a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, and especially low threshold voltages. Features.

Example 19 a) Electro-optical liquid crystal system containing a liquid crystal mixture consisting of the following compounds: 16.9% p-trans-4-propylcyclohexylbenzonitrile; 13.7% p-trans-4- Butylcyclohexylbenzonitrile; 22.5% p-trans-4-pentylcyclohexylbenzonitrile; 14.5% p-trans-4-heptylcyclohexylbenzonitrile; 5.6% 4- (trans-4-pentyl) 4.8% of 4-pentyl-4 "-cyanoterphenyl; 6.4% of 4- (trans-4-butylcyclohexylcarboxylic acid 4- (trans) cyclohexyl) cyclohexylcarboxylic acid 4- (trans-4-propylcyclohexyl) phenyl -4-propylcyclohexyl) phenyl; 5.6% of 4- (g Lance-4-pentylcyclohexyl) -4′-cyanobiphenyl; 10.0% of 1- [4- [trans-4- (trans-
4-propylcyclohexyl) cyclohexyl] phenyl] -2- (4-cyanophenyl) ethane. b) The electro-optical systems produced by the method described in Example 1b) are characterized by good manufacturability, a wide operating temperature range, advantageous values for electro-optical parameters and their temperature dependence, and good contrast.

Reference Example 61 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical properties: 14.4% p-trans-4-propylcyclohexylbenzonitrile; 2% p-trans-4-butylcyclohexylbenzonitrile; 20% p-trans-4-pentylcyclohexylbenzonitrile; 12% p-trans-4-heptylcyclohexylbenzonitrile; 5.6% 4- ( Trans-4-pentylcyclohexyl) cyclohexylcarboxylate 4- (trans-4-propylcyclohexyl) phenyl; 4.8% of 4-pentyl-4 "-cyanoterphenyl; 6.4% of trans-4-butylcyclohexylcarboxylate 4- (trans-4-propylcyclohexyl) phenic acid 5.6% 4- (trans-4-pentylcyclohexyl) -4′-cyanobiphenyl; 10% 4- (trans-4-propylcyclohexyl) -4′-difluoromethoxybiphenyl; 10% 4- ( Trans-4-pentylcyclohexyl) -4′-difluoromethoxybiphenyl; clearing point TC = 102.3 ° C. viscosity η = 31 mm ² / sec (20 ° C.) optical anisotropy Δn = 0.15 (20 ° C., 589 nm) Dielectric anisotropy Δε = 11.4 (20 ° C., 1 kHz) b) The electro-optical system manufactured by the method described in Example 1b) has good manufacturability, a wide operating temperature range, electro-optical parameters and their temperatures. It is characterized by advantageous values for the dependence, low threshold voltages and good contrast.

Reference Example 62 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical properties: 15.0% p-trans-4-propylcyclohexylbenzonitrile; 0% p-trans-4-butylcyclohexylbenzonitrile; 20.0% p-trans-4-pentylcyclohexylbenzonitrile; 12.0% p-trans-4-heptylcyclohexylbenzonitrile; 6.0% 4- (trans-4-pentylcyclohexyl) -4'-cyanobiphenyl; 6.0% of 4- (trans-4-propylcyclohexyl) phenyl trans-4-butylcyclohexylcarboxylate; 5.0% of 4- Pentyl-4 "-cyanoterphenyl; 6.0% of trans-4- (trans-4- Emissions chill) cyclohexyl carboxylic acid 4- (trans-4-propyl) phenyl; 20.0% of 1- (trans-4-pentylcyclohexyl) -2- (3-fluoro-4-phenyl) ethane.

Clearing point TC = 76.3 ° C. Viscosity η = 30 mm ² / sec (20 ° C.) Optical anisotropy Δn = 0.130 (20 ° C., 589 nm) Dielectric anisotropy Δε = 13 (20 ° C., 1 kHz) b) The electro-optical system produced by the method described in Example 1 b) has good manufacturability, a wide operating temperature range, advantageous values for the electro-optical parameters and their temperature dependence, good contrast, and good contrast. It is characterized by low angle dependence.

Reference Example 63 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical properties: 25% of 2- (4-cyanophenyl) -5-propylpyridine; 25 % Of 2- (4-cyanophenyl) -5-butylpyridine; 25% of 2- (4-cyanophenyl) -5-pentylpyridine; 25% of 2- (4-cyanophenyl) -5- (4- Pentylphenyl) pyridine.

Clearing point TC = 85 ° C. Viscosity η = 70 mm ² / sec (20 ° C.) Optical anisotropy Δn = 0.269 (20 ° C., 589 nm) Dielectric anisotropy Δε = 24.1 (1 kHz, 20 ° C) ordinary refractive index n0 = 1.529 (20 ° C, 589 nm) b) Examples 1b), 1.1, 1.2, 1.3 and 2
The electro-optical system is manufactured by the method described in (1). However, in a method according to 1.1, the ratio of liquid crystal to NOA65 was chosen to be 1: 1 and a 10 μm spacer was used.

In FIG. 1, the relative transmittance of the electro-optical system manufactured by the method described in Examples 1b) and 1.1 was measured by applying an applied voltage [sine wave AC voltage (effective value), frequency: 100 Hz].
As a function of This system is characterized by a particularly good contrast and a low threshold voltage.

Reference Example 64 a) An electro-optical liquid crystal system containing a liquid crystal mixture consisting of the following compounds: 15% p-trans-4-propylcyclohexylbenzonitrile; 15% p-trans-4-butylcyclohexylbenzonitrile 20% p-trans-4-pentylcyclohexylbenzonitrile; 10% 2- (4-cyanophenyl) -5-pentylpyridine; 15% 2- (4-cyanophenyl) -5- (4-pentyl Phenyl) pyridine; 7.5% 4-ethoxy-4'-fluorotolan; 7.5% 4-butoxy-4'-fluorotolan. b) The electro-optical systems produced by the method described in Example 1b) are characterized by good manufacturability, a wide operating temperature range, advantageous values for the electro-optical parameters, low threshold voltages, and especially high stability.

Reference Example 65 a) An electro-optical liquid crystal system containing a liquid crystal mixture consisting of the following compounds: 17.5% of 4-propyl-4'-cyanobiphenyl; 17.5% of 4-butyl-4'- 17.5% of 4-pentyl-4'-cyanobiphenyl; 17.5% of 2- (4-cyanophenyl) -5- (4-
Pentylphenyl) pyridine; 15.0% 4- (trans-4-propylcyclohexyl) -4′-trifluoromethoxytran; 15.0% 4-propyl-4′-trifluoromethoxytran. b) The electro-optical systems produced by the method described in Example 1b) are characterized by a wide operating temperature range, good manufacturability, advantageous values for the electro-optical parameters, low threshold voltages, and especially high stability. .

Example 20 a) An electro-optical liquid crystal system containing a liquid crystal mixture consisting of the following compounds: 15% p-trans-4-propylcyclohexylbenzonitrile; 15% p-trans-4-butylcyclohexylbenzonitrile 15% p-trans-4-pentylcyclohexylbenzonitrile; 15% p-trans-4-heptylcyclohexylbenzonitrile; 10% 2- (3,4-difluorophenyl) -5-propylpyrimidine; 10% 2- (4-fluorophenyl) -5-pentylpyrimidine; 10% 1- [4- (4-propylphenyl) phenyl] -2- (4-cyanophenyl) ethane; 10% 1- [4- (4-pentylphenyl) phenyl] -2- (4-cyanophenyl) ethane. b) The electro-optical systems produced by the method described in example 1b) are characterized by a wide operating temperature range, good manufacturability, advantageous values for the electro-optical parameters, low threshold voltages, and especially high stability. .

Example 21 a) Electro-optical liquid crystal system containing a liquid crystal mixture consisting of the following compounds: 15% p-trans-4-propylcyclohexylbenzonitrile; 15% p-trans-4-butylcyclohexylbenzonitrile 15% p-trans-4-pentylcyclohexylbenzonitrile; 15% p-trans-4-heptylcyclohexylbenzonitrile; 10% 1- (5-propylpyridinyl-2) -2-
(4-cyanophenyl) ethane; 10% of 1- (5-pentylpyridinyl-2) -2-
(4-cyanophenyl) ethane; 8% of 4-fluorophenyl trans-4- (trans-4-propylcyclohexyl) cyclohexylcarboxylate; 8% of trans-4- (trans-4-pentylcyclohexyl) cyclohexylcarboxylic acid 4 -Fluorophenyl; 4% 3,4-difluorophenyl trans-4- (trans-4-pentylcyclohexyl) cyclohexylcarboxylate.

B) The electro-optical system produced by the method described in Example 1 b) has a wide operating temperature range, good manufacturability, advantageous values for the electro-optical parameters, a low threshold voltage and a particularly high stability. Features.

Example 22 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical properties: 17.5% of 2- (4-cyanophenyl) -5-propylpyridine 17.5% 2- (4-cyanophenyl) -5-butylpyridine; 17.5% 2- (4-cyanophenyl) -5-pentylpyridine; 17.5% 2- (4-cyano) Phenyl) -5- (4-
15.0 1- [4- (4-propylphenyl) phenyl] -2- (4-cyanophenyl) ethane; 15.0 1- [4- (4-pentylphenyl) phenyl] Clearing point TC = 94 ° C. Optical anisotropy Δn = 0.2722 (20 ° C., 589 n)
m) Dielectric anisotropy Δε = 25.6 (20 ° C., 1 kHz) b) The electro-optical system manufactured by the method described in Example 1b) has a wide operating temperature range, good manufacturability, and electro-optical parameters. It is characterized by advantageous values and especially low threshold voltages.

Reference Example 66 a) An electro-optical liquid crystal system comprising a liquid crystal mixture consisting of the following compounds and having the following physical properties: 20.0% of 2- (4-cyanophenyl) -5-propylpyridine 20.0% 2- (4-cyanophenyl) -5-butylpyridine; 20.0% 2- (4-cyanophenyl) -5-pentylpyridine; 20.0% 2- (4-cyanophenyl) Phenyl) -5- (4-
Pentylphenyl) pyridine; 10.0% 4- (trans-4-propylcyclohexyl) -3 ′, 4′-difluorobiphenyl; 10.0% 4- (trans-4-pentylcyclohexyl) -3 ′, 4 '-Difluorobiphenyl; clearing point TC = 86 ° C. optical anisotropy Δn = 0.2436 (20 ° C., 589 nm) ordinary refractive index n0 = 1.5259 (20 ° C., 589 nm) dielectric anisotropy Δε = 21 0.8 (1 kHz, 20 ° C.) b) Examples 1b), 1.1, 1.2, 1.3 and 2
The electro-optical system is manufactured by the method described in (1). However, in a method according to 1.1, the ratio of liquid crystal to NOA65 was chosen to be 1: 1 and a 10 μm spacer was used.

In FIG. 2, the relative transmittance of the electro-optical system manufactured by the method described in Examples 1b) and 1.1 was measured by applying an applied voltage [sine wave AC voltage (effective value), frequency: 100 Hz].
As a function of

This system is characterized by a low threshold voltage, advantageous values for the gradient of the electro-optical properties and high UV stability.

[Brief description of the drawings]

FIG. 1 is a diagram showing a relative transmittance of an electro-optical system as an example of an electro-optical liquid crystal containing a liquid crystal mixture of the present invention ( Reference Example 63 ) as a function of voltage.

FIG. 2 is a diagram showing the relative transmittance of an electro-optical system of another example ( Reference Example 66 ) containing the liquid crystal mixture of the present invention as a function of voltage.

──────────────────────────────────────────────────の Continuation of front page (73) Patent holder 591032596 Frankfurter Str. 250, D-64293 Darmstadt, Federal Republic of Germany (72) Inventor: Marden, Shirley, United Kingdom BH 148 8 Tee Dawset Pool Parkstone Lingwood Road 244 (72) Inventor Smith, Graham, UK BH 17 Eighth Pool Canford Heath Henbury Close 10 (72) Inventor Finkenzeller, Ulrich Germany Day-6831 Plan Gstadt Waltopfürth 74 (72) Inventor Leifenrath, Volker Germany Day-6101 Rosddorf Järnstraße 18 (72) Inventor Hitich, Reinhardt, Germany Day-6101 Modautal 1 am Kirchberg 11 (72) Inventor Wilhelm, Stephans, DEー -6100 Darmstadt August-Bebel-Schuttlese 11 (56) References JP-A-2-32067 (JP, A) JP-A-2-274794 (JP, A) JP-A-3-62887 (JP, A) JP-A-1-131144 (JP, A) JP-A-61-66 (JP, A) JP-A-62-167758 (JP, A) JP-A-63-185936 (JP, A) JP-T-63-502114 (JP, A) European Patent Application Publication 313053 (EP, A2) (58) Fields investigated (Int. Cl. ⁷ , DB name) C09K 19/42 G02F 1/13 500 CA (STN) CAOLD (STN) REGISTRY (STN)

Claims (29)

(57) [Claims] 1. A method comprising the steps of: (a) providing a dielectrically positive liquid crystal mixture and further an optically transparent medium between two electrodes optionally provided on a support sheet, wherein the liquid crystal molecules are oriented randomly with the power off; And one of the refractive indices of the liquid crystal mixture essentially corresponds to the refractive index n _{M of the} optically transparent medium , and / or the mass of the liquid crystal mixture divided by the mass of the optically transparent medium is In an electro-optic liquid crystal system having a transmittance in one of the two switching states lower than in the other two states, irrespective of the polarization of the incident light, and irrespective of the polarization of the incident light, the liquid crystal mixture has the formula I ] (Wherein Q ¹ is Wherein ring A ¹ and ring A ² are independently trans-1,4
-Cyclohexylene, 1,4-phenylene, 2-fluoro-1,4-phenylene, 3-fluoro-1,4-phenylene and A ¹ and, if present, one of A ² are pyridine-2 , 5-diyl, pyrimidine-2,5
-Diyl, 1,3-dioxane-2,5-diyl, tetrahydropyran-2,5-diyl or naphthalene-
Z ¹ and Z ² are each independently a single bond, —CH ₂ CH ₂
-, - COO -, - OCO -, - C≡C -, - CH 2 O
- or is Ru two or more thereof der these bridges group, exist
Any one of -CH ₂ CH ₂ -is present, Y and X are each independently H or F, and one of X and Y is also Cl; W is -CN; R ¹ represents one or two non-adjacent CH ₂ groups as —O
-Or -CH = alkyl having from 1 to 12 C atoms, which can also be replaced by CH-, and m is 0, 1 or 2). Electro-optical liquid crystal system. 2. The system according to claim 1, wherein the liquid-crystal mixture is embedded in an optically transparent medium in the form of delimited sections. 3. The system according to claim 1, wherein the liquid crystal mixture forms a coherent continuous phase in an optically transparent medium. 4. The system according to claim 2, wherein the system is a PDLC system. 5. The system according to claim 2, wherein the system is an NCAP system. 6. The PN system according to claim 3, wherein:
The system described in 1. 7. The liquid crystal mixture of the formula Ia (Wherein, ring A ³ and ring A ⁴ are, independently of each other, 1,4-cyclohexylene, 1,4-phenylene, 2-fluoro-1,4
-Phenylene or 3-fluoro-1,4-phenylene, and R ¹ has the meaning of claim 1, X ¹ is H or F, and a combination 1 of the following numbers:
５5 applies to n, Z ³ and Z ⁴ : A system according to any one of the preceding claims, comprising one or more compounds of the formula: 8. The compound of claim Ia wherein: Is The system of claim 7, wherein 9. The liquid crystal mixture comprises the following compounds: Wherein ring C is trans-1,4-cyclohexylene or 1,4-phenylene, and R ¹ has the meaning given in claim 1) and a dielectric anisotropic In order to increase the property, (Wherein, Is 2-fluoro-1,4-phenylene or 3-fluoro-1,4-phenylene, and ring D is trans-1,4-cyclohexylene, 1,4-
Phenylene, 2-fluoro-1,4-phenylene or 3-fluoro-1,4-phenylene, and o is 0 or 1, and R ¹ has the meaning given in claim 1). The system according to any one of claims 1 to 7, comprising 5 to 60% by weight of the above compound. 10. The liquid crystal mixture of the formula Ib [Wherein Q ² is And one of ring A ⁵ and ring A ⁶ is Wherein V ¹ is N or H, and the other, if present, is trans-1,4-cyclohexylene or 1,4-phenylene; and X ² and Y ² are independent of each other H is F or F, P is 0 or 1, and Z ⁵ and Z ⁶ are, independently of one another, a single bond or —CH ₂ CH ₂ — and R
¹ a system according to any one of claims 1 to 7, characterized in that it contains one or more compounds of the meaning indicated in Claim 1. 11. The system according to claim 10, wherein at least one of X ² and Y ² is F. 12. The system according to claim 10, wherein X ² = Y ² = H. 13. The liquid crystal mixture of the formula Ic Wherein Q ³ is And one of ring A ⁷ or ring A ⁸ is (Where T ¹ is —CH ₂ — or —O—) and the other, if present, is trans-1,4-
Cyclohexylene or 1,4-phenylene, 2-fluoro-1,4-phenylene or 3-fluoro-1,4
-Phenylene, Z ⁷ and Z ⁸ are each independently a single bond, -COO-,
—OCO— or —CH ₂ CH ₂ —, r and q are each independently 0 or 1, X ³ is F or Cl, and Is 2-fluoro- or 2-chloro-1,4-phenylene or 3-fluoro- or 3-chloro-1,4-phenylene, and R ¹ has the meaning given in claim 1]. The system according to any one of claims 1 to 7, comprising the above compound. 14. The liquid crystal mixture of the formula Id (Wherein ring A ⁹ is 1,4-phenylene or trans-1,4-
Ring A ¹⁰ is 1,4-phenylene, 2-fluoro-1,4-
Phenylene, 3-fluoro-1,4-phenylene or trans-1,4-cyclohexylene, wherein Z ⁹ is a single bond, —COO—, —OCO— or —CH ₂ C
H ₂ —, Z ¹⁰ is a single bond, —COO— or —CH ₂ CH ₂ —, and s is 0 or 1, and R ¹ is as defined in claim 1). The system according to any one of claims 1 to 7, comprising at least one compound. 15. The liquid crystal mixture of the formula IdE2-1 and IdE3-1 to IdE3-8. (In the formula, R ¹ has the meaning given in claim 1) System according to claim 14, characterized in that it contains one or more compounds selected from the group of compounds. 16. The liquid crystal mixture of the formulas Ie4-1 to Ie4-1.
4-4 (Wherein ring A ¹¹ is in each case independently of one another 1,4-
Phenylene, 2-fluoro-1,4-phenylene, 3-
Fluoro-1,4-phenylene or trans-1,4
-Cyclohexylene, wherein ring A ¹² is independently of one another in each case T is 0 or 1, and Is 2-fluoro-1,4-phenylene or 3-fluoro-1,4-phenylene, and R ¹ is
8. A system according to any one of claims 1 to 7, characterized in that it comprises one or more tri- or tetracyclic compounds selected from the group of the carbononitriles of the meaning given in (1). . 17. A compound of the formula If (Wherein at least one of ring A ¹³ and, if present, ring A ¹⁴ is 1,4-phenylene, 2-fluoro-1,4-phenylene, 3-fluoro-1,4-phenylene, trans-
1,4-cyclohexylene, pyridine-2,5-diyl, pyrimidine-2,5-diyl or 1,3-dioxane-2,5-diyl and the other, if present, trans-1,4. -Cyclohexylene, 1,4-
Phenylene, Z ¹¹ and Z ¹² independently of one another in each case a single bond, -C≡C-, -CH ₂ CH _2- , -COO-,-
OCO- or a combination of two or more of these bridge members; v is 0, 1 or 2; a is 0 or 1; Is 2-fluoro-1,4-phenylene or 3-fluoro-1,4-phenylene; Is 3,5-difluoro-1,4-phenylene, and T ² is —Cl, —F, —CF ₃ , —OCF ₃ , —OC
8. A system according to any one of claims 1 to 7, characterized in that it comprises one or more compounds of HF ₂ or NCS and R ¹ has the meaning given in claim 1). . 18. The system according to claim 17, wherein T ² is NCS. 19. The system according to claim 17, wherein T ² is —F, —CF ₃ , —OCF ₃ or —OCHF ₂ . 20. The system according to claim 17, wherein T ² is Cl. 21. The system according to claim 20, wherein v is 1 or 2. 22. The liquid-crystal mixture as claimed in claim 1, wherein the dielectrically positive component A comprises Δε > 2.
2. A method according to claim 1, further comprising a dielectrically neutral compound B consisting of a compound of .ltoreq..DELTA..epsilon. 8. The system according to any one of 7 above. 23. The liquid-crystal mixture of the formula Ig R ¹ -Q ⁴ -COO-Q ⁵ -R ² Ig wherein Q ⁴ and Q ⁵ are in each case independently of one another And one of Q ⁴ and Q ⁵ is And R ¹ and R ² each independently of one another have the meaning given for R ¹ in claim 1). The system according to any one of claims 1 to 7. 24. The liquid-crystal mixture of the formula IhR ¹ -Q ⁶ -C≡CQ ⁷ -R ² Ih wherein at least one of the radicals R ¹ and R ² is as defined for R ¹ in claim 1. One of the two groups R ¹ and R ² is F, Cl, OCF ₃ , O
It is also CHF ₂ or CF ₃ , and the radicals Q ⁶ or Q ⁷ are in each case independently of one another And Q ⁶ is And Q ⁷ is The system according to any one of claims 1 to 7, wherein the system comprises one or more compounds. 25. The liquid crystal mixture of the formula Ii R ¹ -Q ⁸ -CH ₂ CH ₂ -Q ⁹ -R ² Ii wherein R ¹ and R ² are each independently of one another.
^And Q ⁸ and Q ⁹ independently of one another in each case trans-1,4-cyclohexylene, 1,4-phenylene, 4,4′-biphenylyl, 4,4 ′ -Cyclohexylphenyl or 4,4 '
-Phenylcyclohexyl (wherein one of the 1,4-phenylene groups present in the molecule can also be replaced by fluorine or chlorine)]. The system according to any one of claims 1 to 7. 26. The liquid crystal mixture according to any one of the compounds II to IV T-W ¹ -Phe-CN II R-W ¹ -Cyc-CN III TV-Phe-CN IV (wherein R is Independently of one another, one or two non-adjacent CH ₂ groups can also be replaced by —O—, —CO— and / or —CH ＝ CH
An alkyl group having 5 C atoms, W ¹ is Phe. (F) -Y ¹ or Cyc-Y ^1, Y ¹ is a single bond, a -COO- or -OCO-, V is pyridine -2,5-diyl or pyrimidine-2,
T is R, R-Phe. (F) -Y ¹ or R-Cyc
Is -Y ^1, and Phe. (F) is 1,4-phenylene, Ri 2-fluoro-1,4-phenylene or 3-fluoro-1,4-phenylene der, Phe is 1,4-phenylene Yes, Cyc is a transformer
The system according to any one of claims 1 to 7, further comprising one or more compounds selected from -1,4-cyclohexylene ). 27. The system according to claim 1, wherein the liquid crystal mixture has a dielectric anisotropy of ΔΔ> 3. 28. The liquid crystal display device according to claim 1, wherein the liquid crystal mixture contains a polychromatic dye.
The system described in the paragraph. 29. The system according to claim 1, wherein the liquid crystal mixture contains a doping component.